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PdI2-Catalyzed Coupling–Cyclization Reactions Involving Two Different 2,3-Allenols: An Efficient Synthesis of 4-(1′,3′-Dien-2′-yl)-2,5-dihydrofuran Derivatives

✍ Scribed by Youqian Deng; Jing Li; Shengming Ma

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 219 KB
Volume: 14
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200800167

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✦ Synopsis

Abstract

Transition‐metal‐catalyzed dimeric coupling–cyclization reactions of two different 2,3‐allenols afforded 4‐(1′,3′‐dien‐2′‐yl)‐2,5‐dihydrofuran derivatives 3. 2‐Substituted 2,3‐allenols 1 cyclized to form the 2,5‐dihydrofuran ring, whereas the 2‐unsubstituted 2,3‐allenols 2 provided the 1,3‐diene unit at the 4‐position. The reaction is proposed to proceed through an oxypalladation, insertion, and β‐hydroxide elimination process. The CC double bond was formed with high E stereoselectivity by β‐hydroxide elimination.

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