@article { ISI:000285370100022, title = {Facile enantioselective synthesis of (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol via proline-catalyzed asymmetric alpha-aminooxylation and alpha-amination of aldehyde}, journal = {Tetrahedron Letters}, volume = {51}, number = {50}, year = {2010}, month = {DEC}, pages = {6565-6567}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A high-yielding enantioselective synthesis of the bioactive (S)-N-(5-chlorothiophene-2-sulfonyl)beta,beta-diethylalaninol (1), a Notch-1-sparing gamma-secretase inhibitor metabolite (with EC50 = 28 nM) effective in reduction of All production in vivo, has been realized starting from readily available 3-pentanone. The key steps of the synthesis are proline-catalyzed alpha-aminooxylation and alpha-amination of aldehyde: the latter contributing an overall yield of 45.2\% and 98\% ee. (C) 2010 Elsevier Ltd. All rights reserved.

}, keywords = {alpha-Amination, alpha-Aminooxylation, Alzheimer{\textquoteright}s disease, Amino alcohol, Proline}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2010.10.029}, author = {Rawat, Varun and Chouthaiwale, Pandurang V. and Chavan, Vilas B. and Suryavanshi, Gurunath and Sudalai, Arumugam} } @article { ISI:000381847500009, title = {Fluoride-assisted synthesis of 1,4,5,6-tetrahydropyridazines via [4+2] cyclodimerization of in situ-generated azoalkenes followed by a C-N bond cleavage}, journal = {Organic Letters}, volume = {18}, number = {16}, year = {2016}, month = {AUG}, pages = {3968-3971}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

An unexpected CsF-assisted C-N bond cleavage was exploited to synthesize highly functionalized and biologically important 1,4,5,6-tetralrydropyridazine derivatives from alpha-halo N-acylhydrazohes in excellent yields. The extrusion of nitrogen and the [4 + 2] cycloaddition between in situ-generated azoalkenes is a key reaction in the process. The identified methodology is suitable for synthesizing a wide variety of analogues of tetrahydropyridazines, which are prevalent in many medicinally important small molecules. The reaction conditions are mild, high-yielding, and amenable for the gram scale.

}, issn = {1523-7060}, doi = {10.1021/acs.orglett.6b01551}, author = {Shelke, Anil M. and Suryavanshi, Gurunath} } @article { ISI:000370108700010, title = {Formal synthesis of pinolide via L-proline-catalyzed sequential alpha-aminooxylation, horner-wadsworth-emmons olefination and sharpless asymmetric dihydroxylation}, journal = {Tetrahedron-Asymmetry }, volume = {27}, number = {2-3}, year = {2016}, month = {FEB}, pages = {142-147}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A convergent, formal enantioselective synthesis of pinolide, a new nonenolide, has been achieved with high enantiomeric purity (99\% ee) starting from readily available raw materials. The main highlight of the synthetic strategy is the application of L-proline catalyzed sequential alpha-aminooxylation and Horner-Wadsworth-Emmons olefination of an aldehyde, Sharpless asymmetric dihydroxylation and Steglich esterification as the key steps for the construction of a key chiral intermediate of the target molecule. (C) 2016 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2016.01.005}, author = {Shelke, Anil M. and Suryavanshi, Gurunath} }