Chiral Broensted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation.

来自 Semantic Scholar

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阅读量：

107

作者：

D Uraguchi，M Terada

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摘要：

It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines. The beneficial effects of the 3,3'-bisaryl substituents of the catalysts on the enantioselectivity are greatly appreciated, and thus 1d functions as an excellent catalyst. The Brønsted acid-catalyzed direct Mannich reactions presented herein provide an attractive way to construct beta-aminoketones under extremely mild conditions. The stereochemical course of this reaction was established through the synthesis of Boc-(S)-phenylglycine methylester. The transformation thus demonstrated is applicable to a useful method for the synthesis of various phenylglycine derivatives.

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关键词：

diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism amines (benzene compounds amino acids, peptides

DOI：

10.1002/chin.200435026

被引量：

1548

年份：

2004