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Highly Enantioselective [3+2] Annulation of Cyclic Enol Silyl Ethers with Donor–Acceptor Cyclopropanes: Accessing 3a ‐Hydroxy [ n .3.0]Carbobicycles
Author(s) -
Xu Hao,
Qu JianPing,
Liao Saihu,
Xiong Hu,
Tang Yong
Publication year - 2013
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.201300032
Subject(s) - enol , silylation , enantioselective synthesis , benzene , annulation , catalysis , chemistry , computer science , service (business) , world wide web , organic chemistry , information retrieval , business , marketing
A new fuse : The title reaction was realized using a new bisoxazoline (BOX)/Cu II catalyst. This reaction works well with cyclic enol silyl ethers of different sizes, and can be extended to dienol and benzene‐fused substrates, thus providing an effective and general access to a range of 3a ‐hydroxy [ n. 3.0]carbobicycles which are found as a core structure in many natural products. TBDPS= tert ‐butyldiphenylsilyl.