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Computer‐Assisted Design of Chiral Boron Enolates: A Novel, Highly Enantioselective Aldol Reaction for Thioacetates and Thiopropionates
Author(s) -
Gennari Cesare,
Moresca Daniela,
Vieth Siegfried,
Vulpetti Anna
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199316181
Subject(s) - aldol reaction , enantioselective synthesis , triethylamine , boron , chemistry , organic chemistry , catalysis
Unsubstituted and anti aldol products with excellent diastereo‐ and enantioselectivity are formed when enolates, generated from the corresponding thioacetates and thiopropionates by using bromoborane 1 and triethylamine, are treated with aldehydes. Bromoborane 1 was designed based on transition state computer modeling and then synthesized.