Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 3, Issue 15, Pages 2741-2749Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b506198a
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A survey of 16 different chiral auxiliaries and a variety of strategies found that an (-)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of aza-[2,3]-Wittig sigmatropic rearrangements with diastereoselectivities of ca. 3 : 1 with respect to the auxiliary. In two specific examples, ca. 50% yields of enantiomerically pure products were obtained after chromatographic purification. These were synthetically manipulated with no erosion of stereochemistry into intermediates that completed formal asymmetric syntheses of (+)- HyMePro and (-)- kainic acid.
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