连续不对称烯丙基取代中的催化剂控制：非天然氨基酸 N,N-二保护基的立体发散性合成。

Catalyst control in sequential asymmetric allylic substitution: stereodivergent access to N,N-diprotected unnatural amino acids.

机构信息

School of Chemistry, University of Leeds, LS2 9JT Leeds, UK.

出版信息

J Org Chem. 2011 Jul 1;76(13):5495-501. doi: 10.1021/jo200720c. Epub 2011 Jun 8.

DOI:10.1021/jo200720c

Abstract

The sequential use of Cu-catalyzed asymmetric allylic alkylation, olefin cross-metathesis, and Ir-catalyzed asymmetric allylic amination allows the concise, stereodivergent synthesis of complex chiral amines with complete regiocontrol and good diastereoselectivity, exemplified by the synthesis of a pair of diastereoisomeric unnatural branched amino acid derivatives.

摘要

铜催化的不对称烯丙基烷基化、烯烃交叉复分解和铱催化的不对称烯丙基氨基化的顺序使用允许通过简洁、立体发散的方法合成具有完全区域控制和良好非对映选择性的复杂手性胺，这可以通过一对非对映异构体的合成来证明不天然支链氨基酸衍生物。