@article { ISI:000227581000010, title = {Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation}, journal = {Tetrahedron}, volume = {61}, number = {11}, year = {2005}, month = {MAR}, pages = {2831-2838}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A simple and effective procedure for the enantioselective synthesis of several beta-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecules and (ii) conversion of cyclic sulfates into the corresponding epoxides using a three-step procedure. (c) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {antihypertensive, asymmetric dihydroxylation, cyclic sulfates, epoxides}, issn = {0040-4020}, doi = {10.1016/j.tet.2005.01.074}, author = {Sayyed, I. A. and Thakur, V. V. and Nikalje, M. D. and Dewkar, Gajanan and Kotkar, S. P. and Sudalai, A.} } @article { ISI:000248356100011, title = {Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines}, journal = {Tetrahedron}, volume = {63}, number = {14}, year = {2007}, month = {APR}, pages = {3026-3030}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient enantioselective synthesis of (S)-timolol has been described using chiral Co-salen-catalyzed kinetic resolution of less expensive (+/-)-epichlorohydrin with 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole in good overall yield (55\%) and excellent enantioselectivity (98\%). Synthesis of (S)-timolol has also been achieved using hydrolytic kinetic resolution as well as asymmetric dihydroxylation routes in 90\% ee and 56\% ee, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

}, keywords = {asymmetric reactions, diols, epoxides, Kinetic resolution, oxazolidinone}, issn = {0040-4020}, doi = {10.1016/j.tet.2007.01.057}, author = {Narina, Srinivasarao V. and Sudalai, Arumugam} } @article { ISI:000272089600022, title = {Enantioselective synthesis of decarestrictine J}, journal = {Tetrahedron Letters}, volume = {50}, number = {51}, year = {2009}, month = {DEC}, pages = {7188-7190}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient total synthesis of decarestrictine J has been achieved using ring-closing metathesis and Yamaguchi esterification as key steps. The stereogenic centres were generated by means of iterative hydrolytic kinetic resolution (HKR) of racemic epoxides. (c) 2009 Elsevier Ltd. All rights reserved.

}, keywords = {Decanolides, epoxides, Hydrolytic kinetic resolution, Ring-closing metathesis, Yamaguchi esterification}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2009.10.035}, author = {Chowdhury, Partha Sarathi and Gupta, Priti and Kumar, Pradeep} } @article { ISI:000271841900023, title = {First asymmetric total synthesis of aspinolide A}, journal = {Tetrahedron Letters}, volume = {50}, number = {50}, year = {2009}, month = {DEC}, pages = {7018-7020}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The first total synthesis of aspinolide A has been achieved using ring-closing metathesis as a key step. The stereogenic centers were generated by means of hydrolytic kinetic resolution (HKR) of racemic epoxides. (C) 2009 Elsevier Ltd. All rights reserved.

}, keywords = {Decanolides, epoxides, Hydrolytic kinetic resolution, Ring-closing metathesis}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2009.09.151}, author = {Chowdhury, Partha Sarathi and Gupta, Priti and Kumar, Pradeep} } @article { ISI:000328606500015, title = {Concise enantioselective syntheses of (+)-L-733,060 and (2S,3S)-3-hydroxypipecolicw acid by cobalt(III)(salen)-catalyzed two-stereocenter hydrolytic kinetic resolution of racemic azido epoxides}, journal = {Synlett}, volume = {25}, number = {1}, year = {2014}, month = {JAN}, pages = {102-104}, publisher = {GEORG THIEME VERLAG KG}, type = {Article}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (99\% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic kinetic resolution of a racemic azido epoxide with two stereocenters and an intramolecular reductive cyclization as key reactions.

}, keywords = {azides, cyclizations, epoxides, piperidines, stereoselective synthesis, Wittig reactions}, issn = {0936-5214}, doi = {10.1055/s-0033-1340074}, author = {Devalankar, Dattatray A. and Chouthaiwale, Pandurang V. and Sudalai, Arumugam} } @article { ISI:000328606500014, title = {One-pot synthesis of cyclic carbonates from aldehydes, sulfur ylide, and CO2}, journal = {Synlett}, volume = {25}, number = {1}, year = {2014}, month = {JAN}, pages = {97-101}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

Treatment of aldehydes with sulfur ylide (CH2=SOMe2 or CH2=SMe2), in the presence of CO2 (1 atm) bubbled sequentially under mild conditions, produces cyclic carbonates in preparative yields. Sodium iodide formed in situ promotes the reaction between epoxide as intermediate and CO2 at ambient conditions, thus constituting a powerful metal-free synthesis of organic cyclic carbonates directly from aldehydes.

}, keywords = {Carbon dioxide, cyclic carbonates, cyclization, epoxides, Insertion}, issn = {0936-5214}, doi = {10.1055/s-0033-1340072}, author = {Aher, Ravindra D. and Kumar, B. Senthil and Sudalai, Arumugam} } @article {45886, title = {Supported imidazole as heterogeneous catalyst for the synthesis of cyclic carbonates from epoxides and CO2}, journal = {Catalysis Communications}, volume = {59}, year = {2015}, month = {JAN }, pages = {201-205}, type = {Article}, abstract = {

Imidazole anchored onto a silica matrix, by means of a propyl linkage, is found to be an effective heterogeneous catalyst for the synthesis of cyclic carbonates from epoxides and CO2 in near quantitative yield. The versatility of this catalyst is demonstrated by using different substrates (epichlorohydrin, propylene oxide, butylene oxide and styrene oxide) for this cycloaddition reaction. These CO2 insertion reactions were typically carried out in the temperature range of 343 to 403 K at 0.6 MPa CO2 pressure under solvent-free conditions. Several spectroscopic methods were used to characterize the catalyst and study the integrity of the fresh and spent catalysts. (C) 2014 Elsevier B.V. All rights reserved.

}, keywords = {Anchored imidazole, CO2 utilization, cyclic carbonates, epoxides}, issn = {1566-7367}, doi = {10.1016/j.catcom.2014.10.026}, author = {Sankar, Meenakshisundaram and Ajithkumar, Thalasseril G. and Sankar, Gopinathan and Manikandan, Palanichamy} } @article { ISI:000369072900005, title = {N-heterocyclic-carbene-catalyzed regioselective oxidative ring-opening of epoxides with aromatic aldehydes: a facile entry to alpha-acyloxyketones}, journal = {Asian Journal of Organic Chemistry}, volume = {5}, number = {1}, year = {2016}, month = {JAN}, pages = {48-51}, publisher = {WILEY-V C H VERLAG GMBH}, address = {POSTFACH 101161, 69451 WEINHEIM, GERMANY}, abstract = {

A high-yielding synthesis of -acyloxyketones using a N-heterocyclic-carbene (NHC)-catalyzed, oxidative ring-opening of epoxides with aromatic aldehydes is described. This regioselective, oxidative process utilizes a N-bromosuccinimide (NBS)/DMSO combination as the oxidant system and Et3N as the base under mild reaction conditions.

}, keywords = {aldehydes, epoxides, halogen oxidants, N-heterocyclic carbenes, oxygen}, issn = {2193-5807}, doi = {10.1002/ajoc.201500355}, author = {Reddi, Rambabu N. and Gontala, Arjun and Prasad, Pragati K. and Sudalai, Arumugam} } @article {46076, title = {Bentonite - Clay - supported cuprous iodide nanoparticles (BENT- CuI NPs): a new heterogeneous catalyst in diversity - oriented synthesis of 1, 2, 3-triazoles in aqueous medium}, journal = {Chemistryselect}, volume = {4}, year = {2019}, month = {JUN }, pages = {7144-7150}, type = {Article}, abstract = {

Bentonite clay supported cuprous iodide nanoparticles (BENT-CuI NPs) were prepared and demonstrated for the first time as an efficient heterogeneous catalyst in diversity oriented, green synthesis of 1,2,3-triazoles by one-pot, three component reaction between alkyl halides, arylboronic acids, or epoxides with alkynes and sodium azide in aqueous medium. The catalyst was characterized by Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP-AES), Energy Dispersive X-ray Spectroscopy(EDS), Scanning Electron Microscopy (SEM), X-Ray Powder Diffraction (XRD), Transmission Electron Microscopy (TEM) as well as Brunauer-Emmett-Teller (BET) techniques and was found to be reusable for five consecutive runs without significant loss of activity.

}, keywords = {1, 2, 3-triazoles, arylboronic acids, click synthesis, epoxides, green chemistry, heterogeneous catalyst}, issn = {2365-6549}, doi = {10.1002/slct.201900421}, author = {Chavan, V, Pramod and Charate, Shrinivas P. and Desai, V, Uday and Rode, V, Chandrashekhar and Wadgaonkar, Prakash P.} } @article {46886, title = {Triazine-based organic polymer-catalysed conversion of epoxide to cyclic carbonate under ambient CO2 pressure}, journal = {Chemistry-An Asian Journal}, volume = {15}, year = {2020}, month = {JUN }, pages = {1683-1687}, type = {Article}, abstract = {

In this work we have achieved epoxide to cyclic carbonate conversion using a metal-free polymeric catalyst under ambient CO2 pressure (1.02 atm) using a balloon setup. The triazine containing polymer (CYA-ANIS) was prepared from cyanuric chloride (CYA-Cl) and o-dianisidine (ANIS) in anhydrous DMF as solvent by refluxing under the N-2 gas environment. The presence of triazine and amine functional groups in the polymer results in the adsorption of CO2 up to 7 cc/g at 273 K. This inspired us to utilize the polymer for the conversion of a series of functionalised epoxides into their corresponding cyclic carbonates in the presence of tetrabutyl ammonium iodide (TBAI) as co-catalyst. The product has wide range of applications like solvent in lithium ion battery, precursor for polycarbonate, etc. The catalyst was efficient for the conversion of different mono and di-epoxides into their corresponding cyclic carbonates under atmospheric pressure in the presence of TBAI as co-catalyst. The study indicates that epoxide attached with electron withdrawing groups (like, CH2Cl, glycidyl ether, etc.) displayed better conversion compared to simple alkane chain attached epoxides. This is mainly due to the stabilization of electron rich intermediates produced during the reaction (e. g. epoxide ring opening or CO2 incorporation into the halo-alkoxide anion). This catalyst mixture was capable to maintain its reactivity up to five cycles without losing its activity. Post catalytic characterization clearly supports the heterogeneous and recyclable nature of the catalyst.

}, keywords = {CO2 fixation, cyclic carbonates, epoxides, Heterogeneouscatalyst, metal free catalyst, Triazinepolymer}, issn = {1861-4728}, doi = {10.1002/asia.201901277, Early Access Date = APR 2020}, author = {Biswas, Tanmoy and Halder, Arjun and Paliwal, Khusboo S. and Mitra, Antarip and Tudu, Gouri and Banerjee, Rahul and Mahalingam, Venkataramanan} }