Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones

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Contents Vol 60(3)

doi:10.1071/CH06412

Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones

Namdev S. Vatmurge ^A, Braja G. Hazra ^A ^B, Vandana S. Pore ^A

^A Organic Chemistry Synthesis Division, National Chemical Laboratory, Pune 411008, India.
^B Corresponding author. Email: bg.hazra@ncl.res.in





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Australian Journal of Chemistry 60(3) 196–204 http://dx.doi.org/10.1071/CH06412
Submitted: 1 November 2006 Accepted: 13 February 2007 Published online: 2 April 2007

Abstract

Six new chiral 1,2-amino alcohol derivatives have been synthesized starting from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. Asymmetric reduction of aryl ketones with in-situ generated oxazaborolidine from these amino alcohol derivatives and BH₃·Me₂S afforded secondary alcohols with good yield and moderate to high enantiomeric excess.