We present here a regiospecific synthesis of 7-alkyl- or 7-aryl-6-hydroxy-1,4-oxazepan-5-ones
and 2-[aryl(hydroxy)methyl]- or 2-(1-hydroxyalkyl)morpholin-3-ones
from a diastereomeric mixture of trans-3-alkyl-
or -3-aryl-N-(2-hydroxyethyl)-N-(1-phenylethyl)oxirane-2-carboxamides.
This chemodivergent synthesis is easily controlled by an appropriate
choice of cyclization reaction conditions.
chemoselectivity - cyclization - alkoxide - oxazepan-5-ones - morpholin-3-ones