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A Chiral N , N′ ‐Dioxide–Zn II Complex Catalyzes the Enantioselective [2+2] Cycloaddition of Alkynones with Cyclic Enol Silyl Ethers
Author(s) -
Kang Tengfei,
Ge Shulin,
Lin Lili,
Lu Yan,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600801
Subject(s) - enantioselective synthesis , enol , cycloaddition , silylation , chemistry , cyclobutene , cyclobutane , silyl enol ether , catalysis , organic chemistry , medicinal chemistry , ring (chemistry)
A highly efficient enantioselective [2+2] cycloaddition between alkynones and cyclic enol silyl ethers was developed by using a chiral N , N′ ‐dioxide‐zinc(II) complex as a catalyst. This method functions well for a variety of terminal alkynes as well as cyclic enol silyl ethers, with good to excellent enantioselectivity (up to 97 % ee ). This is also the first successful example for the catalytic enantioselective [2+2] cycloaddition of internal alkynes with cyclic enol silyl ethers to give fully substituted cyclobutenes. Meanwhile, the desired cyclobutene product can easily be transformed into fused cyclobutane derivatives.