Enantioselective Organocatalytic Aminomethylation of Aldehydes: a Role for Ionic Interactions and Efficient Access to Beta2-amino Acids

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2006 May 25

PMID 16719457

Citations 8

Authors

Yonggui Chi

Samuel H Gellman

Affiliations

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Abstract

Organocatalytic Mannich addition of aldehydes to a formaldehyde-derived iminium species catalyzed by proline-derived chiral pyrrolidines provides beta-amino aldehydes with >/=90% ee. Mechanistic analysis of the proline-catalyzed reactions suggests that non-hydrogen-bonded ionic interactions at the Mannich reaction transition state can influence stereochemical outcome. The beta-amino aldehydes from our process bear a substituent adjacent to the carbonyl and can be efficiently converted to protected beta2-amino acids, which are important building blocks for beta-peptide foldamers that display useful biological activities.

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