Dynamic Kinetic Resolution of β-Azido Alcohols. An Efficient Route to Chiral Aziridines and β-Amino Alcohols
- 9 May 2001
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (11) , 4022-4025
- https://doi.org/10.1021/jo015579d
Abstract
Enzymatic resolution of β-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic β-azido alcohols were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and conversion up to 98%). The synthetic utility of this procedure has been illustrated by the practical synthesis of (S)-propanolol I and (R)-β-azido-α-(4-methoxyphenyl)ethanol ((R)-1c), a direct precursor of denopamine II.Keywords
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