通过腈类化合物便捷合成稳定的醛亚胺 - 硼烷配合物、手性δ-氨基醇和γ-取代的γ-氨基丁酸类似物。

Convenient synthesis of stable aldimine-borane complexes, chiral delta-amino alcohols, and gamma-substituted GABA analogues from nitriles.

作者信息

Ramachandran P Veeraraghavan, Biswas Debanjan

机构信息

Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.

出版信息

Org Lett. 2007 Aug 2;9(16):3025-7. doi: 10.1021/ol0710919. Epub 2007 Jul 14.

DOI:10.1021/ol0710919

PMID:17630752

Abstract

A one-pot synthesis of stable aldimine-trialkylborane adducts, the first synthesis of C- and N-deuterated imine-borane complexes, and their application for a highly enantioselective (84-99% ee) synthesis of delta-amino alcohols and gamma-substituted gamma-aminobutyric acids, including deuterated amino acids from nitriles, are described.

摘要

描述了一种一锅法合成稳定的醛亚胺 - 三烷基硼烷加合物，首次合成碳和氮氘代的亚胺 - 硼烷配合物，以及它们在高度对映选择性（84 - 99% ee）合成δ - 氨基醇和γ - 取代的γ - 氨基丁酸（包括来自腈的氘代氨基酸）中的应用。