Abstract
A new BINOL-derived chiral bifunctional phosphine has been designed and successfully prepared, which features a cyclic substructure of 1,3,5-diazaphosphinane. This chiral phosphine possesses good air stability in solid state, and it can be conveniently used as a relatively more nucleophilic phosphine organocatalyst. Preliminary investigations showed that it could generally afford fair to excellent yields but only modest enantioselectivity in the (aza)-Morita–Baylis–Hillman reactions of activated olefins such as ethyl acrylate and methyl vinyl ketone with aldehydes or imines.
[Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus Sulfer and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]
GRAPHICAL ABSTRACT
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Acknowledgments
Financial support from the National Natural Science Foundation of China (Grant Nos. 20672057, 21121002) is gratefully acknowledged.