Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine

被引:151
作者
Chen, G [1 ]
Tokunaga, N [1 ]
Hayashi, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo, Kyoto 6068502, Japan
关键词
D O I
10.1021/ol0507367
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acaC)(C2H4)(2) and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones in over 99% ee. This asymmetric reaction was applied to the synthesis of (R)-tolterodine.
引用
收藏
页码:2285 / 2288
页数:4
相关论文
共 56 条
[1]  
Amengual R, 2002, SYNLETT, P1791
[2]   Asymmetric total synthesis of (+)-tolterodine, a new muscarinic receptor antagonist, via copper-assisted asymmetric conjugate addition of aryl Grignard reagents to 3-phenyl-prop-2-enoyl-oxazolidinones [J].
Andersson, PG ;
Schink, HE ;
Österlund, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8067-8070
[3]   A rapid catalytic asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines [J].
Belyk, KM ;
Beguin, CD ;
Palucki, M ;
Grinberg, N ;
DaSilva, J ;
Askin, D ;
Yasuda, N .
TETRAHEDRON LETTERS, 2004, 45 (16) :3265-3268
[4]   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
[5]   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
[6]   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
[7]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[8]   A new efficient route to totterodine [J].
Botteghi, C ;
Corrias, T ;
Marchetti, M ;
Paganelli, S ;
Piccolo, O .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (04) :379-383
[9]   Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors [J].
Defieber, C ;
Paquin, JF ;
Serna, S ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (21) :3873-3876
[10]   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