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Complete π-Facial Stereoselectivity in the TiCl4-Mediated [4 + 2] Cycloaddition of Cyclopentadiene to N,N′-fumaroyldi[(2R)-bornane-10,2-sultam]

✍ Scribed by Christian Chapius; Piotr Rzepecki; Tomasz Bauer; Janusz Jurczak

Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
417 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Under the co‐operative influence of two prosthetic groups, and independent of the TiCl~4~ concentration, complete and constant diastereofacial π‐selection was achieved during the [4 + 2] cycloaddition of cyclopentadiene to N,N′‐fumaroyl‐di[(2__R__)‐bornane‐10,2‐sultam] ((−)‐1c); reactive conformations are discussed.

📜 SIMILAR VOLUMES

Stereoselectivity in the TiCl4-Catalyzed
Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters
✍ Michal Achmatowicz; Christian Chapuis; Piotr Rzepecki; Janusz Jurczak 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 German ⚖ 134 KB 👁 2 views

The [4 2] cycloaddition of cyclopentadiene to the (2R )-bornane-10,2-sultam derivative (À)-1b of fumaric monomethyl ester proceeds with high endo and p-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl 4 . The major diastereoisomer endo-(2R,3R )-2b, isolated in 87% yield by cryst