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Direct Synthesis of 6-Azabicyclo[3.2.1]oct-6-en-2-ones and Pyrrolizidines from Divinyl Ketones and Observation of Remarkable Substituent Effects

✍ Scribed by Xianxiu Xu; Yifei Li; Yu Zhang; Lingjuan Zhang; Ling Pan; Qun Liu

Book ID: 101422790
Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 185 KB
Volume: 353
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.201000880

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✦ Synopsis

Abstract

Substituents create access to molecular diversity. Under basic conditions, 6‐azabicyclo[3.2.1]oct‐6‐en‐2‐ones 3 and pyrrolizidines 4 are efficiently synthesized, respectively, in a single step from ethyl isocyanoacetate 2 and divinyl ketones 1 bearing an aryl or alkyl group at the 2‐position. For comparison, only the corresponding pyrrolizidines 4′ can be obtained from divinyl ketones 1′ bearing a methoxycarbonyl group at the 2‐position.

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