A New BINOL-Derived Chiral Bifunctional Phosphine Organocatalyst: Preparation and Application in Asymmetric (Aza)-Morita-Baylis-Hillman Reactions

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.

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GRAPHICAL ABSTRACT

Keywords:

• Chiral phosphine
• bifunctional organocatalyst
• Morita–Baylis–Hillman reaction
• asymmetric catalysis

Acknowledgments

Financial support from the National Natural Science Foundation of China (Grant Nos. 20672057, 21121002) is gratefully acknowledged.