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Stereoselective aldol reactions. Reaction of chiral ester titanium enolate with aldehydes

✍ Scribed by YiBin Xiang; Eric Olivier; Nathalie Ouimet

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
216 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

Abstracf

The cbml ester 7 was evoked under TiC/JEf,N cond@ons and reacted wth aldehydes to give moderas to good sfereoselectrvrbes The c/m/ auxhary group can be removed by ample sapon~ffcafm and recovered

πŸ“œ SIMILAR VOLUMES

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Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes
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A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastereoselectivities (up to 99:1) and isolated yields (94%).

Reaction of achiral titanium Z-enolates
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Aldol reactions between the putative Z-enolate derived from 2-methyl-3-pentanone and several chiral ot-tert-butyldiphcnylsilyioxy aldehydes have been studied. The stereoehemical outcome suggests that stereoelectronic effects play a dominant role in these reactions and the results can be accommodated