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Aza-annulation of enaminones with crotonyl chloride — Formal reversal of regioselectivity

✍ Scribed by James P. Murphy; Mark Hadden; Paul J. Stevenson

Book ID: 104207997
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 429 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00755-2

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✦ Synopsis

The regtochemist~' of aza-annulation of enaminones with ct,l~-unsaturated acid chlorides Ioearing hydrogen atoms on the y-carbon is reversed s~hen triethylamine is used as mediator. When the reaction was carried out at lower temperatures a 3-acyl J:Ly-unsaturated compound could be isolated which ~clised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent.

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