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Gold(I)‐Catalyzed Desymmetrization of 1,4‐Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement
Author(s) -
Wu Hongmiao,
Zi Weiwei,
Li Guigen,
Lu Hongjian,
Toste F. Dean
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201503357
Subject(s) - desymmetrization , enantioselective synthesis , chemistry , claisen rearrangement , catalysis , tandem , bicyclic molecule , yield (engineering) , stereochemistry , organocatalysis , ring (chemistry) , organic chemistry , combinatorial chemistry , materials science , composite material , metallurgy
An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4‐dienes under the catalysis of ( S )‐DTBM‐Segphos(AuCl) 2 /AgBF 4 . This reaction system was highly selective for the formation of 3,3‐rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6‐ and 6,7‐fused ring systems.