@article { ISI:000228575900005, title = {Asymmetric dihydroxylation route to (R)-(-)-octopamine, (R)-(-)-tembamide and (R)-(-)-aegeline}, journal = {Arkivoc}, number = {3}, year = {2005}, month = {JAN}, pages = {36-43}, publisher = {ARKAT USA INC}, type = {Article}, address = {C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}, abstract = {

A simple and efficient asymmetric synthesis of (R)-(-)-octopamine 1, (R)-(-)-tembamide 2 and (R)-(-)-aegeline 3 is described for the first time employing the Sharpless asymmetric dihydroxylation (AD) as the source of chirality. (C) 2004 Elsevier Science Ltd. All rights reserved.

}, keywords = {aegeline, Asymmetric synthesis, Dihydroxylation, octopamine, tembamide}, author = {Sadyandy, R. and Fernandes, R. A. and Kumar, P.} } @article { ISI:000237405000023, title = {Co-catalyzed reductive cyclization of azido and cyano substituted alpha,beta-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram}, journal = {Tetrahedron}, volume = {62}, number = {20}, year = {2006}, month = {MAY}, pages = {4907-4916}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Sodium borohydride in combination with a catalytic amount of CoCl, has been found to be an excellent catalytic system in reductive cyclizations of suitably substituted azido and cyano groups of alpha,beta-unsaturated esters to afford gamma and delta-lactams in high yields. The process has been demonstrated for the enantioselective synthesis of (R)-baclofen, (R)-rolipram, and (R)-4-fluorophenylpiperidinone, a key intermediate for (-)-paroxetine. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {Asymmetric synthesis, cobalt chloride, gamma and delta-lactams, reduction, sodium borohydride}, issn = {0040-4020}, doi = {10.1016/j.tet.2006.03.017}, author = {Paraskar, A. S. and Sudalai, A.} } @article { ISI:000237937900022, title = {Enantioselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone, novel cytokine modulators via sharpless asymmetric epoxidation and L-proline catalyzed mannich reaction}, journal = {Tetrahedron}, volume = {62}, number = {24}, year = {2006}, month = {JUN}, pages = {5756-5762}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A short and efficient enantioselective synthesis of (-)-cytoxazone and its stereoisomer (+)-epi-cytoxazone, novel cytokine modulators, has been described with good yield and enantioselectivity. Ti-catalyzed Sharpless asymmetric epoxidation of allyl alcohol and L-proline catalyzed three-component Mannich reaction constitute the key steps in introducing stereogenicity into the molecule. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {aminohydroxylation, Asymmetric synthesis, epoxidation, Mannich reaction, Oxidation, Ozonolysis}, issn = {0040-4020}, doi = {10.1016/j.tet.2006.03.079}, author = {Paraskar, Abhimanyu S. and Sudalai, Arumugam} } @article { ISI:000241179400021, title = {Short enantioselective synthesis of (-)-chloramphenicol and (+)-thiamphenicol using tethered aminohydroxylation}, journal = {Tetrahedron}, volume = {62}, number = {43}, year = {2006}, month = {OCT}, pages = {10202-10207}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient enantioselective synthesis of (-)-chloramphenicol (1) and (+)-thiamphenicol (2) is described. These antibiotics have been synthesized from commercially available 4-nitrobenzaldehyde and 4-(methylthio)benzaldehyde, respectively, using tethered amino-hydroxylation and Sharpless asymmetric epoxidation as the chirality inducing steps. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {asymmetric epoxidation, Asymmetric synthesis, Kinetic resolution, Tethered aminohydroxylation}, issn = {0040-4020}, doi = {10.1016/j.tet.2006.08.019}, author = {George, Shyla and Narina, Srinivasarao V. and Sudalai, Arumugarn} } @article { ISI:000262312300018, title = {First asymmetric total synthesis of penarolide sulfate A(1)}, journal = {European Journal of Organic Chemistry}, number = {36}, year = {2008}, month = {DEC}, pages = {6213-6224}, publisher = {WILEY-BLACKWELL}, type = {Article}, address = {COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA}, abstract = {

Penarolide sulfate A(1), with three contiguous stereogenic centers on a macrocyclic skeleton, affords promise as an alpha-glucosidase inhibitor. Herein, we describe the first asymmetric total synthesis of this natural product. A stereoselective strategy for rapid assembly of the complete framework of the 30-membered macrocyclic core is delineated herein. Sequential amidation and intramolecular Sonogashira cross-coupling reactions were pivotal to the success of our efforts. ((C) Wiley-VCH Verlag GmbH \& Co. KGaA, 69451 Weinheim, Germany, 2008)

}, keywords = {Asymmetric synthesis, C-C coupling, Dihydroxylation, epoxidation, Macrocycles, Regioselectivity, Total synthesis}, issn = {1434-193X}, doi = {10.1002/ejoc.200800680}, author = {Mohapatra, Debendra K. and Bhattasali, Debabrata and Gujar, Mukund K. and Khan, Mohammad Islam and Shashidhara, K. S.} } @article { ISI:000285311000016, title = {Enantio- and diastereocontrolled total synthesis of (+)-strictifolione}, journal = {European Journal of Organic Chemistry}, number = {36}, year = {2010}, month = {DEC}, pages = {6993-7004}, publisher = {WILEY-BLACKWELL}, address = {COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA}, abstract = {

A concise and practical enantioselective synthesis of (+)-strictifolione has been achieved in high diastereomeric excess using Jacobsen{\textquoteright}s hydrolytic kinetic resolution, proline-catalyzed sequential alpha-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde and cross olefin/ring-closing metathesis as the key steps.

}, keywords = {Asymmetric synthesis, Hydrolytic kinetic resolution, lactones, Natural products, organocatalysis, Ring-closing metathesis, Total synthesis}, issn = {1434-193X}, doi = {10.1002/ejoc.201001221}, author = {Kumar, Pradeep and Pandey, Menaka and Gupta, Priti and Naidu, S. Vasudeva and Dhavale, Dilip D.} } @article { ISI:000297523700048, title = {Bidentate ligand-catalyzed enantioselective addition of RZnX to benzaldehyde}, journal = {Tetrahedron Letters}, volume = {52}, number = {48}, year = {2011}, month = {NOV}, pages = {6501-6503}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

{Enantioselective addition of RZnX (R = alkyl

}, keywords = {1, 2-Addition, Asymmetric synthesis, Chelating ligands, Organozinc}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2011.09.120}, author = {Jagtap, Ravindra S. and Joshi, Navalkishore N.} } @article { ISI:000297791400001, title = {Organocatalytic asymmetric 1,6-addition reactions}, journal = {Chemcatchem}, volume = {3}, number = {12}, year = {2011}, month = {DEC}, pages = {1847-1849}, publisher = {WILEY-BLACKWELL}, address = {COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA}, keywords = {Asymmetric synthesis, catalysis, Michael addition, organocatalysis, phase-transfer catalysis}, issn = {1867-3880}, doi = {10.1002/cctc.201100279}, author = {Biju, Akkattu T.} } @article { ISI:000346161500008, title = {Protecting-group-free diastereoselective total synthesis of (+/-)-6-epi-cleistenolide and chemoenzymatic synthesis of (-)-6-epi-cleistenolide}, journal = {European Journal of Organic Chemistry}, number = {36}, year = {2014}, month = {DEC}, pages = {8049-8054}, publisher = {WILEY-V C H VERLAG GMBH}, address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY}, abstract = {

A short, efficient, practical, and protecting-group-free diastereoselective total synthesis of (+/-)-6-epi-cleistenolide (1) has been achieved in five steps in 60\% overall yield. The use of a chemoenzymatic approach also gave (-)-6-epi-cleistenolide (1) (\>99.9\% ee). The Achmatowicz reaction, chemoselective oxidation of a hemiacetal, diastereoselective 1,3-anti reduction of alpha-hydroxy ketone, and enzymatic resolution of a 1,3-diol are the key features of this linear total synthesis. The synthetic strategy demonstrated in this paper could be extended for an asymmetric total synthesis of (-)-cleistenolide (1) and related biologically active natural products.

}, keywords = {Asymmetric synthesis, diastereoselectivity, Enzyme catalysis, Lipases, Oxygen heterocycles, Total synthesis}, issn = {1434-193X}, doi = {10.1002/ejoc.201403123}, author = {Mahajan, Pankaj S. and Gonnade, Rajesh G. and Mhaske, Santosh B.} } @article { ISI:000348245000002, title = {Comprehensive study on the effect of acid additives in 1(R),2(R)-Bis[(S)-prolinamido]cyclohexane catalyzed direct asymmetric aldol reactions in aqueous media}, journal = {Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry}, volume = {54}, number = {1}, year = {2015}, month = {JAN}, pages = {84-92}, publisher = {COUNCIL SCIENTIFIC \& INDUSTRIAL RES}, address = {ANUSANDHAN BHAWAN, 2 RAFI MARG, NEW DELHI, 110001, INDIA}, abstract = {

The catalytic efficacy of (1R,2R)-bis[(S)-prolinamido]cyclohexane 1, prepared from the readily available natural amino acid L-proline has been studied for the direct asymmetric aldol reaction of cyclohexanone with substituted benzaldehydes at room temperature in presence of various acid additives. A wide variety of acids e.g. aliphatic fatty acid, chiral acid, sulphonic acid, aromatic acid, etc. have been used as additive for the aldol reaction in aqueous media. A loading of 10 mol\% of catalyst 1 is employed in this reaction, and good yields (up to 98\% yield), diastereoselectivity (up to 96\% de) and enantioselectivities (up to 87\% ee) can be achieved in aqueous media within very short reaction time (1-4 hours).

}, keywords = {acid additives, aqueous media, Asymmetric synthesis, direct aldol reaction, organocatalysis}, issn = {0376-4699}, author = {Bhowmick, Sudipto and Kunte, Sunita S. and Bhowmick, Kartick C.} } @article { ISI:000354982900007, title = {Concise enantioselective synthesis of naturally active (S)-3-hydroxypiperidine}, journal = {Synthetic Communications}, volume = {45}, number = {13}, year = {2015}, month = {APR}, pages = {1559-1565}, publisher = {TAYLOR \& FRANCIS INC}, address = {530 WALNUT STREET, STE 850, PHILADELPHIA, PA 19106 USA}, abstract = {

A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed -aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97\% ee) and high overall yield (38\%).

}, keywords = {Asymmetric synthesis, bioactivity, Enantioselectivity, Natural products, organocatalysis}, issn = {0039-7911}, doi = {10.1080/00397911.2015.1033428}, author = {Dey, Soumen and Karabal, Pratibha U. and Sudalai, Arumugam} } @article { ISI:000350056800015, title = {Proline-catalyzed alpha-aminooxylation of beta-amino aldehydes: access to enantiomerically pure syn- and anti-3-amino-3-aryl-1,2-alkanediols}, journal = {Synlett}, volume = {26}, number = {3}, year = {2015}, month = {FEB}, pages = {355-358}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

A new synthetic method for enantioselective synthesis of syn 3-amino-3-aryl-1,2-alkanediols via praline catalyzed alpha-aminaoxn y ylation of beta-amino aldehydes des are described. This methodology is successfully applied to a concise and protecting group-free asymmetric synthesis of (-)-cytoxazone (+)-epi-cytoxazone and formal synthesis of N-thiolated 2-oxazolidinone.

}, keywords = {amino aldehydes, Asymmetric synthesis, catalysis, diastereoselectivity, Enantioselectivity, Natural product}, issn = {0936-5214}, doi = {10.1055/s-0034-1379735}, author = {Venkataramasubramanian, V. and Kiran, I. N. Chaithanya and Sudalai, Arumugam} } @article { ISI:000371239900016, title = {Enantioselective modular total synthesis of macrolides Sch725674 and C-4-epi-Sch725674}, journal = {European Journal of Organic Chemistry}, number = {6}, year = {2016}, month = {FEB}, pages = {1215-1226}, publisher = {WILEY-V C H VERLAG GMBH}, address = {POSTFACH 101161, 69451 WEINHEIM, GERMANY}, abstract = {

The convergent total synthesis of Sch725674 has been accomplished by starting from (R)-1,2-epoxyheptane and assembling five modules in a highly stereoselective manner to give the final product in 6.6\% overall yield. The same strategy was extended to the synthesis of its C-4 epimer. Key reactions of the synthetic pathway include a Jacobsen hydrolytic kinetic resolution of an epoxide followed by its regioselective opening through a Yamaguchi-Hirao alkynylation, and ring-closing metathesis reaction to furnish the unique 14-membered ring macrolactone. In addition, the influence of protecting groups on the efficiency of the ring-closing metathesis (RCM) macrocyclization has been studied to maximize its yields.

}, keywords = {Asymmetric synthesis, Hydrolytic kinetic resolution, Macrocycles, Metathesis, Natural products}, issn = {1434-193X}, doi = {10.1002/ejoc.201501531}, author = {Sharma, Brijesh M. and Gontala, Arjun and Kumar, Pradeep} } @article {46353, title = {Concise formal synthesis of (-)-(6R,11R,14R)-colletallol via D-proline catalysed alpha-aminooxylation-Wittig olefination strategy}, journal = {Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry}, volume = {58}, year = {2019}, month = {SEP}, pages = {1029-1036}, type = {Article}, abstract = {

An efficient enantioselective formal synthesis of marine macrolide (-)-(6R,11R,14R)-colletallol has been achieved starting from commercially available raw materials. The key reactions include the D-proline catalyzed a-aminooxylation of aldehyde followed by Horner-Wardsworth-Emmons olefination in a sequential fashion to give the macrolide key intermediate 5 in high enantiomeric purity (97\% ee) and high overall yield (32\%).

}, keywords = {alpha-aminoxylation, Asymmetric synthesis, Enantioselectivity, Natural products, organocatalysis}, issn = {0376-4699}, author = {Dey, Soumen and Gadakh, Sunita and Sudalai, Arumugam} } @article {46718, title = {Vinylogous michael addition of 3-alkylidene-2-oxindoles to beta,gamma-unsaturated alpha-keto esters by bifunctional cinchona alkaloids}, journal = {European Journal of Organic Chemistry}, volume = {2020}, year = {2020}, month = {SEP }, pages = {5690-5694}, type = {Article}, abstract = {

A highly enantioselective vinylogous Michael addition of 3-alkylidene-2-oxindoles with beta,gamma-unsaturated alpha-keto esters using a bifunctional tertiary-amine thiourea catalyst is demontsrated. The challenging Michael reaction with the beta,gamma-unsaturated alpha-keto esters has been accomplished due to the synchronized H-bond guided dual activation of vinylogous nucleophile and electrophile by catalyst. The reaction afforded product in high yield while resulting in excellent stereocontrol (\> 19:1E/Zand upto 99 \%ee).

}, keywords = {3-Alkylidene-2-oxindoles, Asymmetric synthesis, beta, gamma-Unsaturated alpha-keto esters, Michael adduct, Vinylogous Michael addition}, issn = {1434-193X}, doi = {10.1002/ejoc.202000835, Early Access Date = SEP 2020}, author = {Jaiswal, Manish K. and Kumar, Rajesh and Singh, Sanjay and Jain, Shailija and Vanka, Kumar and Singh, Ravi P.} } @article {47676, title = {Ni-catalyzed highly enantioselective synthesis of sulfur protected P-stereogenic supramolecular phosphine}, journal = {Journal of Chemical Sciences}, volume = {133}, year = {2021}, month = {DEC}, pages = {119}, type = {Article}, abstract = {As phosphines readily invert, the synthesis of P-chiral phosphines is a challenging task and has been rarely investigated. We report the synthesis of a nickel complex [Ni-((S,S)Me-FerroLANE)(phenyl)(I)] (Ni-Cat.1) and its performance in a P-C coupling reaction to generate P-chiral phosphine. The Ni-Cat.1 was synthesized by mixing ligand (S,S) Me-FerroLANE with the metal precursor [(diphenylphosphanyl)nickel(phenyl)(I)] in good yield. Ni-Cat.1 was characterized using different spectroscopic and analytical techniques. Treatment of racemic methyl(phenyl)phosphine (1) with 1-(3-iodophenyl)urea (2) produced the corresponding P-chiral supramolecular phosphine (3). Optimization of reaction parameters produced sulfur protected phosphine N-(3-(methyl(phenyl)phosphorothioyl)phenyl)formamide (3{\textquoteright}) with excellent enantiomeric excess (99\% ee) and moderate conversion (51\%).}, keywords = {Asymmetric synthesis, Nickel catalyst, P-C coupling, P-Stereogenic phosphine, supramolecular ligands}, issn = {0974-3626}, doi = {10.1007/s12039-021-01978-3}, author = {Koshti(S), Vijay S. and Chandanshive, Amol C. and Mote, Nilesh R. and Chikkali, Samir H.} }