Ruthenium-Catalyzed Isomerization/(Transfer) Hydrogenation of Allylic Alcohols

被引:0
作者
Yang, Shuang [1 ]
Fang, Xinqiang [1 ]
机构
[1] Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Peoples R China
来源
SYNTHESIS-STUTTGART | 2025年 / 57卷 / 16期
基金
中国国家自然科学基金;
关键词
allylic alcohol; hydrogenation; transfer hydrogenation; redox isomerization; ruthenium catalyst; ASYMMETRIC TRANSFER HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; MOLECULAR CATALYSTS; KINETIC RESOLUTION; CARBONYL-COMPOUNDS; CHIRAL LIGANDS; TANDEM; KETONES; REDUCTION; PRECURSOR;
D O I
10.1055/a-2589-4376
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylic alcohols, renowned for their reactivity in epoxidation, dihydroxylation, allylic substitution, and isomerization, stand as pivotal intermediates in organic synthesis. While numerous reviews have delved into the above transformations of allylic alcohols, a significant void remains in the comprehensive discussion of their conversion into saturated alcohols under (transfer) hydrogenation conditions. This short review endeavors to fill that void by highlighting the tandem isomerization/(transfer) hydrogenation of allylic alcohols facilitated by ruthenium catalysts. We hope that this account will advance the understanding and application of allylic alcohols in (transfer) hydrogenation, fostering innovation and discovery in this critical area. 1 Introduction 2 Ruthenium-Catalyzed Conversion of Allylic Alcohols into Saturated Alcohols under Transfer Hydrogenation Conditions 3 Ruthenium-Catalyzed Conversion of Allylic Alcohols into Saturated Alcohols under Hydrogenation Conditions 4 Conclusion
引用
收藏
页码:2423 / 2433
页数:11
相关论文
共 85 条
[1]   Asymmetric homogeneous hydrogenations at scale [J].
Ager, David J. ;
de Vries, Andre H. M. ;
de Vries, Johannes G. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3340-3380
[2]   Allylic alcohols as synthetic enolate equivalents: Isomerisation and tandem reactions catalysed by transition metal complexes [J].
Ahlsten, Nanna ;
Bartoszewicz, Agnieszka ;
Martin-Matute, Belen .
DALTON TRANSACTIONS, 2012, 41 (06) :1660-1670
[3]   Isomerization-Asymmetric Hydrogenation Sequence Converting Racemic β-Ylidenecycloalkanols into Stereocontrolled β-Substituted Cycloalkanols Using a Ru Catalytic System with Dual Roles [J].
Arai, Noriyoshi ;
Okabe, Yuki ;
Ohkuma, Takeshi .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (24) :5540-5547
[4]   Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions [J].
Bartlett, Samuel L. ;
Johnson, Jeffrey S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) :2284-2296
[5]   Iridium- Catalyzed Asymmetric Hydrogenation of 3,3-Disubstituted Allylic Alcohols in Ethereal Solvents [J].
Bernasconi, Maurizio ;
Ramella, Vincenzo ;
Tosatti, Paolo ;
Pfaltz, Andreas .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (09) :2440-2444
[6]   APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF (R)-4-METHOXYDALBERGIONE AND (S)-4-METHOXYDALBERGIONE VIA ASYMMETRIC CATALYTIC-HYDROGENATION [J].
BISSEL, P ;
SABLONG, R ;
LEPOITTEVIN, JP .
TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :835-838
[7]   Ruthenium-Catalyzed One-Pot Tandem Isomerization-Transfer Hydrogenation Reactions of γ-Trifluoromethylated Allylic Alcohols and β-Trifluoromethylated Enones [J].
Bizet, Vincent ;
Pannecoucke, Xavier ;
Renaud, Jean-Luc ;
Cahard, Dominique .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) :1394-1402
[8]  
Blacker A J., 2010, ASYMMETRIC CATALYSIS, P265, DOI DOI 10.1002/9783527630639.CH16
[9]   DIRECTED HOMOGENEOUS HYDROGENATION [J].
BROWN, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (03) :190-203
[10]   Ruthenium-catalyzed isomerizations of allylic and propargylic alcohols in aqueous and organic media: Applications in synthesis [J].
Cadierno, Victorio ;
Crochet, Pascale ;
Gimeno, Jose .
SYNLETT, 2008, (08) :1105-1124