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A Nonconcerted Intramolecular Diels-Alder Reaction of Chiral Allenic-Acid Derivatives

✍ Scribed by Latchezar S. Trifonov; Alexander S. Orahovats

Publisher: John Wiley and Sons
Year: 1989
Tongue: German
Weight: 395 KB
Volume: 72
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19890720108

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✦ Synopsis

The reaction between the chiral allenic acid (+)-(S)-1 and the carbodiimides 2 a 4 and the keten-imine 6 gives, under mild conditions, the tricyclic compounds >5,7, and 8. Low diastereoselectivity and a partial loss of optical activity are observed. A stepwise mechanistic pathway oiu a biradical intermediate is postulated.

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