Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 10, Pages 2071-2074Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc08813e
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- Croatian Ministry of Science, Education and Sports
- Ruder Boskovic Institute
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The first organocatalytic asymmetric addition of thiols to N-acyl ketimines, which are generated in situ from 3-hydroxy isoindolinones, is described. The reaction proceeds smoothly with a broad range of ketimines and thiols using a chiral Bronsted acid catalyst to afford N(acyl),S-acetals comprising a tetrasubstituted stereocenter in high yields and enantioselectivities (up to 98.5 : 1.5 e.r.). The usefulness of the developed protocol is demonstrated in the synthesis of a known HIV-1 reverse transcriptase inhibitor.
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