Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid Derivatives
- 4 December 2001
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (1), 67-77
- https://doi.org/10.1021/ja016838j
Abstract
Methodology for the practical synthesis of nonnatural amino acids has been developed through the catalytic, asymmetric alkylation of α-imino esters and N,O-acetals by enol silanes, ketene acetals, alkenes, and allylsilanes using chiral transition metal-phosphine complexes as catalysts (1−5 mol %). The alkylation products, which are prepared with high enantioselectivity (up to 99% ee) and diastereoselectivity (up to 25:1/anti:syn), are protected nonnatural amino acids that represent potential precursors to natural products and pharmaceuticals. A kinetic analysis of the catalyzed reaction of alkenes with α-imino esters is presented to shed light on the mechanism of this reaction.This publication has 77 references indexed in Scilit:
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