Dynamic kinetic resolution of beta-azido alcohols. An efficient route to chiral aziridines and beta-amino alcohols.
Enzymatic resolution of beta-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic beta-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)-beta-azido-alpha-(4-methoxyphenyl)ethanol ((R)-1c), a direct precursor of denopamine II.
Pàmies
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Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.
Bäckvall
J E
JE