Regioselective Nickel-Catalyzed Reductive Couplings of Enones and Allenes

被引:22
作者
Li, Wei [1 ]
Chen, Nan [1 ]
Montgomery, John [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
基金
美国国家科学基金会;
关键词
allenes; conjugate addition; nickel; reductive coupling; regioselectivity; TRANSFER HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; 2-COMPONENT ADDITION; REVERSE PRENYLATION; CONJUGATE ADDITION; CARBONYL-COMPOUNDS; FORM 1,3-DIENES; SIMPLE ALKENES; ALKYNES; CYCLIZATIONS;
D O I
10.1002/anie.201004740
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkenes made easy: In a complement to coupling processes of terminal alkynes, the reductive coupling of enones and allenes provides access to conjugate addition products that possess a 1,1-disubstituted alkene (see scheme; cod=1,5-cyclooctadiene). The solvent composition and reducing agent must be carefully matched to allow high levels of regioselectivity to be observed. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8712 / 8716
页数:5
相关论文
共 60 条
[1]   Enantioselective total synthesis of (+)-testudinariol A using a new nickel-catalyzed allenyl aldehyde cyclization [J].
Amarasinghe, KKD ;
Montgomery, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9366-9367
[2]   Structure of an η1 nickel O-enolate:: Mechanistic implications in catalytic enyne cyclizations [J].
Amarasinghe, KKD ;
Chowdhury, SK ;
Heeg, MJ ;
Montgomery, J .
ORGANOMETALLICS, 2001, 20 (03) :370-372
[3]  
[Anonymous], 2004, ANGEW CHEM
[4]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[5]  
Bower J. F., 2009, ANGEW CHEM, V121, P36
[6]   Catalytic C-C coupling via transfer hydrogenation: Reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level [J].
Bower, John F. ;
Skucas, Eduardas ;
Patman, Ryan L. ;
Krische, Michael J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15134-+
[7]   Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents [J].
Bower, John F. ;
Kim, In Su ;
Patman, Ryan L. ;
Krische, Michael J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :34-46
[8]   Allenes and transition metals: A diverging approach to heterocycles [J].
Brummond, KM ;
Mitasev, B .
ORGANIC LETTERS, 2004, 6 (13) :2245-2248
[9]   Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].
Brummond, KM ;
Kent, JL .
TETRAHEDRON, 2000, 56 (21) :3263-3283
[10]   Cobalt-catalyzed reductive coupling of activated alkenes with alkynes [J].
Chang, Hong-Tai ;
Jayanth, Thiruvellore Thatai ;
Wang, Chun-Chih ;
Cheng, Chien-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :12032-12041