期刊
TETRAHEDRON LETTERS
卷 47, 期 2, 页码 145-148出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.10.154
关键词
chiral quaternary ammonium bifluorides; cyclic enones; enol silyl ethers; Michael addition; gamma-nitro ketones; silyl nitronates
Highly enantio selective Michael addition of silyl nitronates to cyclic alpha,beta-unsaturated ketones has been accomplished by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bifluoride 1 as an efficient catalyst, offering a new route to the enol silyl ethers of optically active gamma-nitro ketones. The synthetic utility of this transformation has been demonstrated by the diastereoselective derivatizations of the optically active enol silyl ethers to the corresponding alpha-substituted cyclic ketones having three consecutive stereochemically defined stercocenters. (c) 2005 Elsevier Ltd. All rights reserved.
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