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

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

The reaction between the chiral allenic acid (+)‐(S)‐1 and the carbodiimides 2a–d and the keten‐imine 6 gives, under mild conditions, the tricyclic compounds 3–5, 7, and 8. Low diastereoselectivity and a partial loss of optical activity are observed. A stepwise mechanistic pathway via a biradical in...

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Veröffentlicht in:Helvetica chimica acta 1989-02, Vol.72 (1), p.59-64
Hauptverfasser: Trifonov, Latchezar S., Orahovats, Alexander S.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung:The reaction between the chiral allenic acid (+)‐(S)‐1 and the carbodiimides 2a–d and the keten‐imine 6 gives, under mild conditions, the tricyclic compounds 3–5, 7, and 8. Low diastereoselectivity and a partial loss of optical activity are observed. A stepwise mechanistic pathway via a biradical intermediate is postulated.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19890720108