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- Title
Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines.
- Authors
Yan, Liang; Xu, Jing ‐ Kun; Huang, Chao ‐ Fan; He, Zeng ‐ Yang; Xu, Ya ‐ Nan; Tian, Shi ‐ Kai
- Abstract
A new strategy has been established for the kinetic resolution of racemic allylic alcohols through a palladium/sulfonyl-hydrazide-catalyzed asymmetric OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % ( S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcohols were smoothly resolved with selectivity factors of more than 400 through an asymmetric allylic alkylation of monosubstituted hydrazines under air at room temperature. Importantly, this kinetic resolution process provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.
- Subjects
RACEMIC mixtures; ENANTIOMERS; HYDRAZINES; HYDRAZIDES; UREA compounds; ALKYLATION
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 37, p13041
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201601747