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

Namdev S. Vatmurge; Braja G. Hazra; Vandana S. Pore

doi:10.1071/CH06412

RESEARCH ARTICLE

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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 and Vandana S. Pore ^A

+ Author Affiliations

- Author Affiliations

^A Organic Chemistry Synthesis Division, National Chemical Laboratory, Pune 411008, India.

^B Corresponding author. Email: bg.hazra@ncl.res.in

Australian Journal of Chemistry 60(3) 196-204 https://doi.org/10.1071/CH06412
Submitted: 1 November 2006 Accepted: 13 February 2007 Published: 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.

Acknowledgments

Namdev S. Vatmurge thanks CSIR, New Delhi, for the award of a Junior Research Fellowship. B. G. Hazra is thankful to CSIR, New Delhi, for the Award of Emeritus Scientist Scheme.

References

^* THF and toluene are expected to give different enantiomeric excesses under a similar range of temperatures. This is because of the very different polarity between THF and toluene. We thank a referee for this point.

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

Abstract

Acknowledgments

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