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Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines
Author(s) -
Yan Liang,
Xu JingKun,
Huang ChaoFan,
He ZengYang,
Xu YaNan,
Tian ShiKai
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601747
Subject(s) - allylic rearrangement , kinetic resolution , chemistry , hydrazide , catalysis , tsuji–trost reaction , hydrazine (antidepressant) , palladium , medicinal chemistry , selectivity , substitution reaction , organic chemistry , enantioselective synthesis , chromatography
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.