1. Palladium‐Catalyzed Asymmetric Hydrosulfonylation of 1,3‐Dienes with Sulfonyl Hydrazides
- Author
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Lei Cheng, Li-Jun Xiao, Qi-Lin Zhou, Jian-Hua Xie, and Ming-Ming Li
- Subjects
Sulfonyl ,chemistry.chemical_classification ,Phosphoramidite ,Allylic rearrangement ,010405 organic chemistry ,Hydrazine ,chemistry.chemical_element ,Regioselectivity ,General Chemistry ,General Medicine ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Catalysis ,0104 chemical sciences ,Sulfone ,chemistry.chemical_compound ,chemistry ,Palladium - Abstract
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.
- Published
- 2020
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