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, José L. G., Barros, David, Maestro, M. Carmen, Slawin, Alexandra M. Z. and Bulman Page, Philip C. (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

Full text not available from this repository.

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 (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User:	Rachel Smith
Date Deposited:	21 Jun 2011 11:38
Last Modified:	24 Sep 2024 10:28
URI:	https://ueaeprints.uea.ac.uk/id/eprint/32819
DOI:	10.1021/jo000494i

Actions (login required)

View Item