Asymmetric amplification in the catalytic enantioselective 1,2-addition of Grignard reagents to enones

被引:23
作者
Caprioli, Francesca [1 ]
Madduri, Ashoka V. R. [1 ]
Minnaard, Adriaan J. [1 ]
Harutyunyan, Syuzanna R. [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
关键词
CARBONYL-COMPOUNDS; TERTIARY ALCOHOLS; KETONES; ALDEHYDES; MECHANISM;
D O I
10.1039/c3cc41892h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Large asymmetric amplification originating from solubility differences between the enantiopure and the racemic catalyst is observed in the addition of Grignard reagents to enones. This behaviour is not reaction or catalyst specific and is observed for metal complexes of a variety of chiral diphosphine ligands, extensively used in asymmetric catalysis.
引用
收藏
页码:5450 / 5452
页数:3
相关论文
共 28 条
[1]   From parity to chirality:: chemical implications revisited [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Jiménez, JL ;
Palacios, JC .
TETRAHEDRON-ASYMMETRY, 2000, 11 (14) :2845-2874
[2]   Asymmetric Addition of Diorganozinc Reagents to Aldehydes and Ketones [J].
Binder, Caitlin M. ;
Singaram, Bakthan .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2011, 43 (02) :139-208
[3]   From a chiral switch to a ligand portfolio for asymmetric catalysis [J].
Blaser, Hans-Ulrich ;
Pugin, Benoit ;
Spindler, Felix ;
Thommen, Marc .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1240-1250
[4]   Catalytic Enantioselective Addition of MeMgBr and Other Grignard Reagents to Aldehydes [J].
Fernandez-Mateos, Emilio ;
Macia, Beatriz ;
Ramon, Diego J. ;
Yus, Miguel .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (34) :6851-6855
[5]   Aluminum-catalyzed asymmetric alkylations of pyridyl-substituted alkynyl ketones with dialkylzinc reagents [J].
Friel, Donna K. ;
Snapper, Marc L. ;
Hoveyda, Amir H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) :9942-9951
[6]  
Girard C, 1998, ANGEW CHEM INT EDIT, V37, P2922
[7]   On the mechanism of the copper-catalyzed enantioselective 1,4-addition of grignard reagents to α,β-unsaturated carbonyl compounds [J].
Harutyunyan, Syuzanna R. ;
Lopez, Fernando ;
Browne, Wesley R. ;
Correa, Arkaitz ;
Pena, Diego ;
Badorrey, Ramon ;
Meetsma, Auke ;
Minnaard, Adriaan J. ;
Feringa, Ben L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) :9103-9118
[8]   Recent progress in the catalytic synthesis of tertiary alcohols from ketones with organometallic reagents [J].
Hatano, Manabu ;
Ishihara, Kazuaki .
SYNTHESIS-STUTTGART, 2008, (11) :1647-1675
[9]   Highly active chiral Phosphoramide-Zn(II) complexes as conjugate acid-base catalysts for enantioselective organozinc addition to ketones [J].
Hatano, Manabu ;
Miyamoto, Takashi ;
Ishihara, Kazuaki .
ORGANIC LETTERS, 2007, 9 (22) :4535-4538
[10]  
JACOBSEN EN, 2004, COMPREHENSIVE ASY S2, V2