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

被引：92

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.

引用

页码：6467 / 6470

页数：4

共 64 条

[21] Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone [J].

Ito, M ;

Kitahara, S ;

Ikariya, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6172-6173

[22] Stereocontrolled synthesis of the 22E,24β(S)-trifluoromethyl steroidal side chain and its application to the synthesis of fluorinated analogues of naturally occurring sterols [J].

Jiang, B ;

Liu, Y ;

Zhou, WS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6231-6236

[23] Synthesis of trifluoromethylated compounds with four consecutive asymmetric centers via sequential [3,3]-Ireland-Claisen rearrangement and iodolactonization [J].

Konno, T ;

Kitazume, T .

TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :223-230

[24] Highly regio- and stereo-controlled Pd(0)-catalyzed nucleophilic substitution reaction for the synthesis of optically active γ-fluoroalkylated allylic alcohols [J].

Konno, T ;

Ishihara, T ;

Yamanaka, H .

TETRAHEDRON LETTERS, 2000, 41 (44) :8467-8472

[25] A novel and expedient synthesis of optically active fluoroalkylated amino acids via palladium-catalyzed allylic rearrangement and Ireland-Claisen rearrangement [J].

Konno, T ;

Daitoh, T ;

Ishihara, T ;

Yamanaka, H .

TETRAHEDRON-ASYMMETRY, 2001, 12 (19) :2743-2748

[26] Stereoselective synthesis of trifluoromethylated compounds via Johnson-Claisen and Eshenmoser-Claisen rearrangements [J].

Konno, T ;

Nakano, H ;

Kitazume, T .

JOURNAL OF FLUORINE CHEMISTRY, 1997, 86 (01) :81-87

[27] Highly stereoselective synthesis of trifluoromethylated compounds via ester-enolate [2,3]-Wittig and [3,3]-Ireland-Claisen rearrangements [J].

Konno, T ;

Umetani, H ;

Kitazume, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :137-150

[28] A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction [J].

Konno, Tsutornu ;

Tanaka, Tornoo ;

Miyabe, Tornotsugu ;

Morigaki, Atsunori ;

Ishihara, Takashi .

TETRAHEDRON LETTERS, 2008, 49 (13) :2106-2110

[29] Highly Enantioselective Asymmetric Isomerization of Primary Allylic Alcohols with an Iridium-N,P Complex [J].

Li, Jia-Qi ;

Peters, Byron ;

Andersson, Pher G. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (40) :11143-11145

[30] Chemoselective Conjugate Reduction of α,β-Unsaturated Ketones Catalyzed by Rhodium Amido Complexes in Aqueous Media [J].

Li, Xuefeng ;

Li, Liangchun ;

Tang, Yuanfu ;

Zhong, Ling ;

Cun, Linfeng ;

Zhu, Jin ;

Liao, Jian ;

Deng, Jingen .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2981-2988

← 1 2 3 4 5 6 7 →