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STEREOSELECTIVE CONSTRUCTION OF QUATERNARY CENTERS AT AMBIENT-TEMPERATURE BY THE HIGHLY STEREOCONTROLLED MIGRATION OF GROUPS CONTAINING SP-HYBRIDIZED,SP(2)-HYBRIDIZED-, AND SP(3)-HYBRIDIZED CARBON-ATOMS

MARSON, CM; WALKER, AJ; PICKERING, J; HOBSON, AD; WRIGGLESWORTH, R; EDGE, SJ; (1993) STEREOSELECTIVE CONSTRUCTION OF QUATERNARY CENTERS AT AMBIENT-TEMPERATURE BY THE HIGHLY STEREOCONTROLLED MIGRATION OF GROUPS CONTAINING SP-HYBRIDIZED,SP(2)-HYBRIDIZED-, AND SP(3)-HYBRIDIZED CARBON-ATOMS. J ORG CHEM , 58 (22) 5944 - 5951.

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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, cyclopropyl, 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 beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.

Type:Article
Title:STEREOSELECTIVE CONSTRUCTION OF QUATERNARY CENTERS AT AMBIENT-TEMPERATURE BY THE HIGHLY STEREOCONTROLLED MIGRATION OF GROUPS CONTAINING SP-HYBRIDIZED,SP(2)-HYBRIDIZED-, AND SP(3)-HYBRIDIZED CARBON-ATOMS
Keywords:PINACOL-TYPE REARRANGEMENT, PRACTICAL ASYMMETRIC-SYNTHESIS, SILYL ETHER REARRANGEMENTS, THREO ALDOLS, KETONES, TRIETHYLALUMINUM, ERYTHRO
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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