@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:000239522700020, title = {Enantioselective synthesis of (S,S)-ethambutol using proline-catalyzed asymmetric alpha-aminooxylation and alpha-amination}, journal = {Tetrahedron-Asymmetry}, volume = {17}, number = {11}, year = {2006}, month = {JUL}, pages = {1738-1742}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient enantioselective synthesis of (S,S)-ethambutol, a tuberculostatic antibiotic, has been achieved in 99\% ee via both proline-catalyzed alpha-aminooxylation and alpha-amination of n-butyraldehyde as the key step. (c) 2006 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2006.06.011}, author = {Kotkar, Shriram P. and Sudalai, Arumugam} } @article { ISI:000251621900034, title = {Efficient organocatalytic route to the atorvastatin side-chain}, journal = {Tetrahedron Letter}, volume = {48}, number = {48}, year = {2007}, month = {NOV}, pages = {8544-8546}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An organocatalytic route to the synthesis of the atorvastatin side-chain, a building block present in the statin family, is described using L-proline-catalyzed alpha-aminooxylation of an aldehyde. The method also employs an iodine-induced intramolecular electrophilic cyclization of a carbonate to produce the iodocarbonate in a highly diastereoselective manner. (C) 2007 Elsevier Ltd. All rights reserved.

}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2007.09.133}, author = {George, Shyla and Sudalai, Arumugam} } @article { ISI:000243630300013, title = {Enantioselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone via Rh-catalyzed diastereoselective oxidative C-H aminations}, journal = {Tetrahedron Letter}, volume = {48}, number = {1}, year = {2007}, month = {JAN}, pages = {65-68}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient enantioselective synthesis of (-)-cytoxazone (1) and (+)-epi-eytoxazone (2) using proline-catalyzed asymmetric alpha-amino-oxylation of aldehydes followed by Rh-catalyzed diastereoselective oxidative C-H amination as the key steps is described. syn or anti 1,2-aminoalcohols were obtained by Rh-catalyzed intramolecular amidation of the C-H bonds of carbamates or sulfamate esters with good to excellent diastereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.

}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.11.016}, author = {Narina, Srinivasarao V. and Kumar, Talluri Siva and George, Shyla and Sudalai, Arumugam} } @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:000279746300009, title = {Enantioselective synthesis of (+)-alpha-conhydrine and (-)-sedamine by L-proline-catalysed alpha-aminooxylation}, journal = {European Journal of Organic Chemistry}, number = {18}, year = {2010}, month = {JUN}, pages = {3437-3444}, publisher = {WILEY-BLACKWELL}, address = {COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA}, abstract = {

An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)-alpha-conhydrine (98\% ee) and (-)-sedamine (95\% ee), by L-proline-catalysed alpha-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.

}, keywords = {alkaloids, Amino acids, Aminooxylation, Enantioselectivity, organocatalysis}, issn = {1434-193X}, doi = {10.1002/ejoc.201000169}, author = {Shaikh, Tanveer Mahamadali and Sudalai, Arumugam} } @article { ISI:000307433600013, title = {Enantioselective synthesis of HIV protease inhibitor amprenavir via Co-catalyzed HKR of 2-(1-azido-2-phenylethyl)oxirane}, journal = {Tetrahedron-Asymmetry}, volume = {23}, number = {11-12}, year = {2012}, month = {JUN}, pages = {898-903}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A short and efficient enantioselective synthesis of the HIV protease inhibitor amprenavir 1 (99\% ee) as well as a formal synthesis of saquinavir 3 have been achieved in high enantiomeric purity starting from commercially available materials. Our strategy mainly comprises a Co-catalyzed two-stereocentred hydrolytic kinetic resolution (HKR) of racemic 2-(1-azido-2-phenylethyl)oxirane as the chirality inducing step. Also presented is a concise synthesis of (S)-3-hydroxytetrahydrofuran 4, the key structural feature, in high enantiomeric purity (98\% ee). (c) 2012 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2012.06.003}, author = {Gadakh, Sunita K. and Reddy, R. Santhosh and Sudalai, Arumugam} } @article { ISI:000355354100007, title = {Enantioselective synthesis of guggultetrol and D-ribo-phytosphingosine tetraacetate via L-proline catalyzed sequential alpha-aminooxylation/Horner-Wardsworth-Emmons olefination-Sharpless asymmetric dihydroxylation strategy}, journal = {Tetrahedron-Asymmetry}, volume = {26}, number = {10-11}, year = {2015}, month = {MAY}, pages = {571-576}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient enantioselective synthesis of two bioactive molecules, that is, guggultetrol and D-ribo-phytosphingosine, is described with high enantioselectivity (\>98\% ee) starting from commercially available 1-hexadecanol. The synthesis comprises organocatalyzed sequential alpha-aminooxylation of an aldehyde followed by Horner-Wardsworth-Emmons olefination and Sharp less asymmetric dihydroxylation as the key chiral inducing steps. For both syntheses, gamma-hydroxy-alpha,beta-unsaturated ester serves as the common intermediate obtained from proline catalysis. (C) 2015 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2015.04.004}, author = {Venkataramasubramanian, V. and Kumar, B. Senthil and Sudalai, Arumugam} }