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.

Computer‐Assisted Design of Chiral Boron Enolates: A Novel, Highly Enantioselective Aldol Reaction for Thioacetates and Thiopropionates / C.M.A. GENNARI, D. MORESCA, S. VIETH, A. VULPETTI. - In: ANGEWANDTE CHEMIE. - ISSN 0044-8249. - 32:11(1993), pp. 1618-1621.

Computer‐Assisted Design of Chiral Boron Enolates: A Novel, Highly Enantioselective Aldol Reaction for Thioacetates and Thiopropionates

C.M.A. GENNARI
Primo
;
1993

Abstract

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.
silyl ketene acetals; beta-hydroxy acids; titanium-carbohydrate complexes; transition structures; enantiomerically pure; achiral aldehydes; optically pure; anti-aldols; acetic-acid; force-field
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/175901
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