Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines

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 hydra...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-09, Vol.22 (37), p.13041-13045
Main Authors: Yan, Liang, Xu, Jing-Kun, Huang, Chao-Fan, He, Zeng-Yang, Xu, Ya-Nan, Tian, Shi-Kai
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
allylic compounds
Asymmetry
Chemistry
Derivatives
Hydrazines
kinetic resolution
Kinetics
Palladium
Reaction kinetics
Selectivity
Strategy
sulfonyl hydrazides
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Summary: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. A kinetic resolution: A range of racemic allylic alcohols were resolved with selectivity factors of >400 through a palladium/sulfonyl‐hydrazide‐catalyzed asymmetric allylation of monosubstituted hydrazines under air at room temperature. The reaction provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201601747