直接有机催化不对称曼尼希反应：以未修饰的醛作为亲核试剂。

The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophiles.

作者信息

Notz Wolfgang, Tanaka Fujie, Watanabe Shin-Ichi, Chowdari Naidu S, Turner James M, Thayumanavan Rajeswari, Barbas Carlos F

机构信息

The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

出版信息

J Org Chem. 2003 Dec 12;68(25):9624-34. doi: 10.1021/jo0347359.

DOI:10.1021/jo0347359

PMID:14656087

Abstract

The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized alpha- and beta-amino acids, beta-lactams, and amino alcohols.

摘要

一篇详尽的报道披露了未修饰醛作为亲核供体在直接催化不对称曼尼希型反应中的前所未有的应用。我们在拓宽基于手性吡咯烷的催化剂在直接不对称曼尼希型反应中的适用性方面所做的努力，实现了功能化α-和β-氨基酸、β-内酰胺和氨基醇的高度非对映和对映选择性及简洁合成。