A highly enantioselective route to either enantiomer of both alpha- and beta-amino acid derivatives.

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作者：

A Córdova，SI Watanabe，F Tanaka，W Notz，CF Barbas

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摘要：

This report describes the unprecedented use of unmodified aldehydes as donors in a catalytic asymmetric Mannich-type reaction. The proline-catalyzed reaction of N-PMP-protected alpha-imino ethyl glyoxylate with unmodified aliphatic aldehydes provided a general and very mild entry to either enantiomer of beta-amino and alpha-amino acids and derivatives in high yield and stereoselectivity. Six of the seven aldehydes studied yielded products with ee values of 99% or greater. The diastereoselectivity of the reaction increased with the bulkiness of the substituents of the aldehyde donor in the order R = Me < Et < i-Pr < n-Pent. In five of the cases studied, excellent syn stereoselectivities were achieved. In addition, the corresponding chiral beta-amino aldehyde adducts can be readily converted to the corresponding amino acid derivatives. Most significantly, this approach provides facile access to substituted beta-lactams.

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关键词：

zearalenone zearalenone-4-beta-D-glucopyranoside wheat LC-MS conjugated mycotoxins

DOI：

10.1021/ja017833p

被引量：

1180

年份：

2002