Ruthenium-Catalyzed Redox Isomerization of Trifluoromethylated Allylic Alcohols: Mechanistic Evidence for an Enantiospecific Pathway

被引：91
作者：
Bizet, Vincent [1 ]
Pannecoucke, Xavier [1 ]
Renaud, Jean-Luc [2 ]
Cahard, Dominique [1 ]
机构：
[1] Univ & INSA Rouen, COBRA, UMR CNRS 6014, F-76821 Mont St Aignan, France
[2] Univ Caen ENSICAEN, LCMT, UMR CNRS 6507, F-14050 Caen, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 26期
关键词：
asymmetric catalysis; fluorine; isomerization; redox chemistry; ruthenium; ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; ASYMMETRIC TRANSFER HYDROGENATION; CARBONYL-COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; PROPARGYLIC ALCOHOLS; CONJUGATE REDUCTION; EFFICIENT CATALYST; KETONES; COMPLEXES;
D O I：
10.1002/anie.201200827
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Transfer news: A synthetic approach to chiral β-CF 3- substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF 3-bearing allylic alcohols by an intramolecular suprafacial enantiospecific 1,3-hydrogen transfer (see scheme). This method was used for the enantioselective synthesis of (S)-CF 3-citronellol. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：6467 / 6470
页数：4
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