High Stereocontrol in Aldol Reaction with Ketones:  Enantioselective Synthesis of β-Hydroxy γ-Ketoesters by Ester Enolate Aldol Reactions with 2-Acyl-2-alkyl-1,3-dithiane 1-Oxides

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 configu...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-09, Vol.65 (19), p.6027-6034
Main Authors: García Ruano, José L, Barros, David, Maestro, M. Carmen, Slawin, Alexandra M. Z, Page, Philip C. Bulman
Format: Article
Language:English
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Summary: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 α-substituted β-hydroxy-γ-ketoesters.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000494i