A ligand-library approach to the highly efficient rhodium/phosphoramidite-catalyzed asymmetric arylation of N,N-dimethyl-sulfamoyl-protected aldimines

被引:156
作者
Jagt, RBC [1 ]
Toullec, PY [1 ]
Geerdink, D [1 ]
de Vries, JG [1 ]
Feringa, BL [1 ]
Minnaard, ADJ [1 ]
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
关键词
arylation; arylboronic acids; asymmetric catalysis; diarylmethylamines; phosphoramiditesy;
D O I
10.1002/anie.200504309
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Small but effective: The title reaction, after microwave-assisted removal of the N,N-dimethylsulfamoyl protecting group, leads to chiral diarylmethyl amines. The use of 1 mol% catalyst and 1.3 equivalents of aryl boronic acid results in excellent yields (up to 98%) and enantioselectivities (up to 95% ee) of the isolated products. acac = acetylacetonate; eth = ethylene. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2789 / 2791
页数:3
相关论文
共 47 条
[1]   QUINONE IMIDES .37. CONVERSION OF PARA-QUINONE DIIMIDES TO INDOLES [J].
ADAMS, R ;
SAMUELS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (20) :5375-5382
[2]   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
[3]   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
[4]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands (vol 5, pg 682, 2003) [J].
Boiteau, JG ;
Imbos, R ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (08) :1385-1385
[5]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[6]  
Bolm C., 2001, ANGEW CHEM, V113, P3382
[7]   Enantioselective addition of aryllithium reagents to aromatic imines mediated by 1,2-diamine ligands [J].
Cabello, N ;
Kizirian, JC ;
Alexakis, A .
TETRAHEDRON LETTERS, 2004, 45 (24) :4639-4642
[8]   Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride [J].
Corey, EJ ;
Helal, CJ .
TETRAHEDRON LETTERS, 1996, 37 (28) :4837-4840
[9]   Synthesis and application in asymmetric C-C bond formation of solution phase ligand libraries of monodentate phosphoramidites [J].
Duursma, A ;
Lefort, L ;
Boogers, JAF ;
de Vries, AHM ;
de Vries, JG ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (12) :1682-1684
[10]   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