Improved catalytic asymmetric carbon-carbon bond formation using combinations of chiral and achiral monodentate ligands

被引:47
作者
Duursma, A [1 ]
Peña, D [1 ]
Minnaard, AJ [1 ]
Feringa, BL [1 ]
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
关键词
D O I
10.1016/j.tetasy.2005.05.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Mixtures of chiral and achiral monodentate phosphoramidite ligands lead to improved enantioselectivity in the rhodium-catalyzed boronic acid addition. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:1901 / 1904
页数:4
相关论文
共 17 条
[1]   High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites [J].
Boiteau, JG ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9481-9484
[2]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands [J].
Boiteau, JG ;
Imbos, F ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (05) :681-684
[3]   Asymmetric activation of conformationally flexible monodentate phosphites for enantioselective hydrogenation [J].
Chen, WP ;
Xiao, JL .
TETRAHEDRON LETTERS, 2001, 42 (49) :8737-8740
[4]   Highly enantioselective conjugate additions of potassium organotrifluoroborates to enones by use of monodentate phosphoramidite ligands [J].
Duursma, A ;
Boiteau, JG ;
Lefort, L ;
Boogers, JAF ;
de Vries, AHM ;
de Vries, JG ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8045-8052
[5]   First examples of improved catalytic asymmetric C-C bond formation using the monodentate ligand combination approach [J].
Duursma, A ;
Hoen, R ;
Schuppan, J ;
Hulst, R ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (17) :3111-3113
[6]   Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates [J].
Hayashi, T ;
Senda, T ;
Takaya, Y ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11591-11592
[7]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[8]   Asymmetric borane reduction using mixtures of homochiral amino alcohol ligands [J].
Kaptein, B ;
Elsenberg, H ;
Minnaard, AJ ;
Broxterman, QB ;
Hulshof, LA ;
Koek, J ;
Vries, TR .
TETRAHEDRON-ASYMMETRY, 1999, 10 (07) :1413-1418
[9]   Rh-catalysed asymmetric hydrogenations with a dynamic library of chiral tropos phosphorus-ligands [J].
Monti, C ;
Gennari, C ;
Piarulli, U .
TETRAHEDRON LETTERS, 2004, 45 (37) :6859-6862
[10]   Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites;: a new combinatorial approach in asymmetric catalysis [J].
Peña, D ;
Minnaard, AJ ;
Boogers, JAF ;
de Vries, AHM ;
de Vries, JG ;
Feringa, BL .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (07) :1087-1089