Enantioselective conjugate addition of phenylboronic acid to enones catalysed by a chiral tropos/atropos rhodium complex at the coalescence temperature

被引:43
作者
Monti, C
Gennari, C
Piarulli, U
机构
[1] Univ Milan, Ctr Eccellenza CISI, Dipartimento Chim Organ & Ind, ISTM,CNR, I-20133 Milan, Italy
[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
关键词
D O I
10.1039/b508832a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly enantioselective rhodium-catalysed conjugate addition of phenylboronic acid to cyclic enones has been achieved using a dynamic library of chiral phosphorus ligands; the tropos/atropos nature of the ligands in the rhodium complex has been characterised via P-31-NMR.
引用
收藏
页码:5281 / 5283
页数:3
相关论文
共 12 条
[1]  
Alexakis A, 2001, SYNLETT, P1375
[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]   Improved catalytic asymmetric carbon-carbon bond formation using combinations of chiral and achiral monodentate ligands [J].
Duursma, A ;
Peña, D ;
Minnaard, AJ ;
Feringa, BL .
TETRAHEDRON-ASYMMETRY, 2005, 16 (11) :1901-1904
[4]   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
[5]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[6]   Tropos or atropos? That is the question! [J].
Mikami, K ;
Aikawa, K ;
Yusa, Y ;
Jodry, JJ ;
Yamanaka, M .
SYNLETT, 2002, (10) :1561-1578
[7]   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
[8]   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
[9]   Mixtures of configurationally stable and fluxional atropisomeric monodentate P ligands in asymmetric Rh-catalyzed olefin hydrogenation [J].
Reetz, MT ;
Li, XG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (19) :2959-2962
[10]   A new principle in combinatorial asymmetric transition-metal catalysis: Mixtures of chiral monodentate P ligands [J].
Reetz, MT ;
Sell, T ;
Meiswinkel, A ;
Mehler, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (07) :790-793