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High Acceleration and Improved Diastereoselectivity of Intramolecular Ene-Type Reactions by Diethylaluminum Chloride. Preliminary Communication

✍ Scribed by Wolfgang Oppolzer; Christian Robbiani

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
241 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The pyrrolidines 2 and 10 were obtained by thermal ene‐reactions at +70° and +180° from the (Z)‐4‐aza‐1, 6‐diene 1 and from the (E)‐4‐aza‐1, 6‐diene 9 in the ratios of 75:25 and 50:50, respectively. On the other hand, these cyclizations proceeded readily in the presence of diethylaluminum chloride at − 78° and − 35° giving in high yield the trans‐pyrrolidine 2 from 1 with 100% and from 9 with 89% diastereoselectivity.

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High Asymmetric Induction in Lewis Acid-Promoted Intramolecular Ene-Type Reactions: A diastereo- and enantioselective synthesis of (+)-α-allokainic acid. Preliminary Communication
✍ Wolfgang Oppolzer; Christian Robbiani; Kurt Bättig 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 229 KB 👁 1 views

## Abstract The monocyclic amino diacid (+)‐α‐allokainic acid **1** has been prepared enantioselectively from the ester of __cis__‐β‐chloroacrylic acid and (−)‐8‐phenylmenthol by a series of four synthetic operations in over 15% yield. The crucial step is the intramolecular ‘ene‐type’ reaction of t