Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized …

…, J Pickering, AD Hobson, R Wrigglesworth…

Index: Marson, Charles M.; Walker, Andrew J.; Pickering, Jane; Hobson, Adrian D.; Wrigglesworth, Roger; Edge, Simon J. Journal of Organic Chemistry, 1993 , vol. 58, # 22 p. 5944 - 5951

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Citation Number: 64

Abstract

A very highly diastereoselective semipinacol rearrangement of 2, 3-epoxy alcohols mediated by tin-(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropy1, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn-and anti-epoxy alcohols affords only a single diastereoisomerically pure 8-hydroxy ketone. Additional advantages ...