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

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

Author information

1
Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu

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.

PMID:
17630752
DOI:
10.1021/ol0710919
[Indexed for MEDLINE]

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