Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines
Huamin Wang,
Xiuzheng Li,
Youshao Tu,
Junliang Zhang
Affiliations
Huamin Wang
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. China; Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. China
Xiuzheng Li
School of Pharmacy, Anhui Medical University, 81 N. Meishan Road, Hefei 230032, P. R.China
Youshao Tu
College of Chemistry and Life Science, Advanced Institute of Materials Science, Changchun University of Technology, 2055 N. Yan'an Avenue, Changchun 130012, P. R. China
Junliang Zhang
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. China; Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. China; Corresponding author
Summary: Over the past decades, asymmetric catalysis has been intensely investigated as a powerful tool for the preparation of numerous chiral biologically active compounds. However, developing general and practical strategies for preparation of both enantiomers of a chiral molecule via asymmetric catalysis is still a challenge, particularly when the two enantiomers of a chiral catalyst are not easily prepared from natural chiral sources. Inspired by the biologic system, we report herein an unprecedented catalytic enantiodivergent Michael addition of pyridazinones to enones by subtle adjustment of achiral amino moiety of dipeptide phosphine catalysts. These two dipeptide phosphine catalysts, P5 and P8, could deliver both enantiomers of a series of N2-alkylpyridazinones in good yields (up to 99%) with high enantioselectivities (up to 99% ee) via the catalyst-controlled enantiodivergent addition of pyridazinones to enones.
