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Palladium‐Catalyzed Asymmetric Hydrosulfonylation of 1,3‐Dienes with Sulfonyl Hydrazides
Author(s) -
Li MingMing,
Cheng Lei,
Xiao LiJun,
Xie JianHua,
Zhou QiLin
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012485
Subject(s) - sulfonyl , chemistry , allylic rearrangement , palladium , regioselectivity , catalysis , sulfone , phosphoramidite , hydrazine (antidepressant) , ligand (biochemistry) , organic chemistry , combinatorial chemistry , alkyl , dna , biochemistry , receptor , chromatography , oligonucleotide
A highly enantio‐ and regioselective hydrosulfonylation of 1,3‐dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity‐determining step.