Practical Synthesis of Optically Active Amino Alcohols via Asymmetric Transfer Hydrogenation of Functionalized Aromatic Ketones

2-Substituted acetophenones such as 2-cyano-, 2-azido-, or 2-nitroacetophenones were effectively reduced with a mixture of HCOOH/N(C2H5)3 containing a chiral Ru(II) catalyst, RuCl[(S,S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine](p-cymene), giving the corresponding optically active alcohols,...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2002-03, Vol.67 (5), p.1712-1715
Main Authors: Watanabe, Masahito, Murata, Kunihiko, Ikariya, Takao
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:2-Substituted acetophenones such as 2-cyano-, 2-azido-, or 2-nitroacetophenones were effectively reduced with a mixture of HCOOH/N(C2H5)3 containing a chiral Ru(II) catalyst, RuCl[(S,S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine](p-cymene), giving the corresponding optically active alcohols, which can be converted to optically active amino alcohols with excellent ee's. Similarly, the reaction of 2-benzoylacetophenone with the same Ru catalyst gave a quantitative yield of the corresponding optically active 1,3-diol with 99% ee.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo011076w