Reaction of achiral titanium Z-enolates with chiral α-silyloxy aldehydes
✍ Scribed by Cristina Esteve; Mònica Ferreró; Pedro Romea; Fèlix Urpí; Jaume Vilarrasa
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 184 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 by the Felkin model, with gauche pentane interactions being less important.
📜 SIMILAR VOLUMES
Titanium-mediated aldol reactions of 1 and (S)-2-tert-butyldiphenylsilyloxy aldehydes ( matched pair) afford syn Felkin diastereomers in excellent yield and absolute stercochemical control. Having established that chain length does not affect the yield of the titanium aldol reactions, we have been a
## 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
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