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Regioselective control of allyllithiums of some heterocycles: α vs γ condensation with aldehydes.

✍ Scribed by Erbana Epifani; Saverio Florio; Giovanni Ingrosso

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 273 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)91380-2

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✦ Synopsis

A procedure for directing the condensation of allyllithiums of benzothiazole, benzoxazole and pyrimidine such as 2 with aldehydes to the a or y position is described.Erythro diasteroselection-is observed in the a regioisomers, There is considerable current interest in the synthetic application of stabilized allylic carbanions. 1The control of a vs y substitution in such anions depends upon the complex interplay between the nature of the stabilizing group, charge delocalisation, steric effects, solvation, the type of electrophile, and the counterion.

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