Journal
TETRAHEDRON LETTERS
Volume 58, Issue 2, Pages 145-151Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.11.114
Keywords
Chiral phosphoric acid; Organocatalysis; N,S-Ketal; Isoindolinone; HIV-1 reverse transcriptase inhibitor
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Funding
- J.C. Bose fellowship (DST, India)
- SERB, DST, India [EMR/2014/ 001165]
- CSIR, New Delhi
- IISER Bhopal
- DST
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The chiral Bronsted acid catalyzed enantioselective 1,2-addition of thiols to in situ generated ketimines, derived from 3-hydroxyisoindolinones, has been studied. The protocol provides a variety of isoindolinone-derived N,S-ketals in up to 98% yield and up to 99% enantioselectivity. The products have been converted to a known non-nucleoside HIV-1 reverse transcriptase inhibitor and a 1,3-thiazine derivative. (C) 2016 Elsevier Ltd. All rights reserved.
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