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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.