High stereocontrol in aldol reaction with ketones: Enantioselective synthesis of beta-hydroxy gamma-ketoesters by ester enolate aldol reactions with 2-acyl-2-alkyl-1,3-dithiane 1-oxides

Ruano, J. L. G., Barros, D., Maestro, M. C., Slawin, A. M. Z. and Bulman Page, P. C. B. (2000) High stereocontrol in aldol reaction with ketones: Enantioselective synthesis of beta-hydroxy gamma-ketoesters by ester enolate aldol reactions with 2-acyl-2-alkyl-1,3-dithiane 1-oxides. Journal of Organic Chemistry, 65 (19). pp. 6027-6034. ISSN 0022-3263

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Abstract

The asymmetric aldol reaction of 1,2-diketones, masked as nonracemic 2-acyl dithiane oxides, with lithium enolates derived from several esters and lactones, proceeds with a high degree of stereocontrol at both carbonyl and enolate prochiral centers, the stereocontrol mainly determined by the configuration of the sulfoxide sulfur atom. The sense of induced stereochemistry observed for ester enolates is different from that seen for lactone enolates. Hydrolysis of the dithiane oxide units of the major diastereoisomerically pure aldol products affords enantiomerically pure tertiary alpha-substituted beta-hydroxy-gamma-ketoesters.

Item Type: Article
Uncontrolled Keywords: asymmetric building-block,c-2-symmetrical,3-dithiane 1-oxides,2-acyl-1,enolsilanes,grignard-reagents,1,3-dithiane 1-oxide,chiral lewis-acids,derivatives,pyruvate esters,copper(ii) complexes,additions
Faculty \ School: Faculty of Science > School of Chemistry
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 12:38
Last Modified: 25 Jul 2018 07:57
URI: https://ueaeprints.uea.ac.uk/id/eprint/32819
DOI: 10.1021/jo000494i

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