Surprising role of aryl halides in nickel-catalyzed reductive aldol reactions

被引:34
作者
Chrovian, Christa C. [1 ]
Montgomery, John [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ol063028+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new nickel-catalyzed method for the reductive aldol addition of acrylates and aldehydes has been developed. An unexpected requirement for an aryl iodide additive was found in the process, and the effect was shown to be linked to an initiation step.
引用
收藏
页码:537 / 540
页数:4
相关论文
共 46 条
[1]   Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction [J].
Arnold, LA ;
Naasz, R ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7244-7254
[2]   Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aidol cyclization [J].
Bocknack, BM ;
Wang, LC ;
Krische, MJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5421-5424
[3]   A NEW PROTOCOL FOR REGIOCONTROLLED AND STEREOCONTROLLED ALDOL REACTIONS THROUGH THE CONJUGATE ADDITION OF DIALKYLBORANES TO ALPHA,BETA-UNSATURATED KETONES [J].
BOLDRINI, GP ;
BORTOLOTTI, M ;
MANCINI, F ;
TAGLIAVINI, E ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5820-5826
[4]   Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].
Cauble, DF ;
Gipson, JD ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111
[5]   Unusual palladium-catalyzed silaboration of allenes using organic iodides as initiators: Mechanism and application [J].
Chang, KJ ;
Rayabarapu, DK ;
Yang, FY ;
Cheng, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :126-131
[6]  
Chapdelaine M.J., 1990, ORG REACT, V38, P225
[7]   Highly diastereo- and enantioselective copper-catalyzed domino reduction/aldol reaction of ketones with methyl acrylate [J].
Deschamp, J ;
Chuzel, O ;
Hannedouche, J ;
Riant, O .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1292-1297
[8]   Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents [J].
Feringa, BL ;
Pineschi, M ;
Arnold, LA ;
Imbos, R ;
de Vries, AHM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2620-2623
[9]  
Fuller NO, 2005, SYNLETT, P1459
[10]   Combined experimental and computational investigation of the mechanism of nickel-catalyzed three-component addition processes [J].
Hratchian, HP ;
Chowdhury, SK ;
Gutiérrez-García, VM ;
Amarasinghe, KKD ;
Heeg, MJ ;
Schlegel, HB ;
Montgomery, J .
ORGANOMETALLICS, 2004, 23 (20) :4636-4646