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Construction of functionalised medium rings by stereospecific expansions of 2,3-epoxy alcohols under mild conditions

Marson, CM; Khan, A; Porter, RA; Cobb, AJA; (2002) Construction of functionalised medium rings by stereospecific expansions of 2,3-epoxy alcohols under mild conditions. TETRAHEDRON LETT , 43 (37) 6637 - 6640.

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Abstract

Ketones are converted with very high stereocontrol into functionalised medium rings incorporating a P-hydroxy ketone assembly via a ring-expansion mediated by tin(IV) chloride at low temperatures; either the threo or the erythro aldol products can be obtained. An asymmetric epoxidation permitted a subsequent highly enantiocontrolled semi-pinacol rearrangement. (C) 2002 Elsevier Science Ltd. All rights reserved.

Type:Article
Title:Construction of functionalised medium rings by stereospecific expansions of 2,3-epoxy alcohols under mild conditions
Keywords:STEREOSELECTIVE CONSTRUCTION, QUATERNARY CARBON, REARRANGEMENT, MIGRATION, EPOXIDES, CENTERS
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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