Discovery and application of doubly quaternized cinchona-alkaloid-based phase-transfer catalysts
Bangping Xiang1, Kevin M Belyk, Robert A Reamer
1Department of Process Chemistry, Merck and Co., Inc. P.O. Box 2000, Rahway, NJ 07065 (USA). bangping_xiang@merck.com.
Abstract:
We report the discovery of novel N,N'-disubstituted cinchona alkaloids as efficient phase-transfer catalysts for the assembly of stereogenic quaternary centers. In comparison to traditional cinchona-alkaloid-based phase-transfer catalysts, these new catalysts afford substantial improvements in enantioselectivity and reaction rate for intramolecular spirocyclization reactions with catalyst loadings as low as 0.3 mol% under mild conditions.
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