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

Deng Youqian | Zendy; Li Jing | Zendy; Ma Shengming | Zendy

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

Author(s) -

Deng Youqian,

Li Jing,

Ma Shengming

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200800167

Subject(s) - stereoselectivity , chemistry , catalysis , ring (chemistry) , double bond , hydroxide , medicinal chemistry , coupling reaction , stereochemistry , combinatorial chemistry , polymer chemistry , organic chemistry

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 CC double bond was formed with high E stereoselectivity by β‐hydroxide elimination.

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