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Asymmetric diels-alder reaction of a chiral allenic ester : enantioselective synthesis of (−)-β-santalene

✍ Scribed by Wolfgang Oppolzer; Christian Chapuis

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
243 KB
Volume
24
Category
Article
ISSN
0040-4039

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A Nonconcerted Intramolecular Diels-Alde
A Nonconcerted Intramolecular Diels-Alder Reaction of Chiral Allenic-Acid Derivatives
✍ Latchezar S. Trifonov; Alexander S. Orahovats 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 German ⚖ 395 KB

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 int