Novel dirhodium tetraprolinate catalysts containing bridging prolinate ligands for asymmetric carbenoid reactions

被引:82
作者
Davies, HML [1 ]
Panaro, SA [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1016/S0040-4039(99)01000-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The D-2-symmetric dirhodium prolinate complex 3 is an effective catalyst for asymmetric vinylcarbenoid and phenylcarbenoid cyclopropanations. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5287 / 5290
页数:4
相关论文
共 16 条
[1]   THE HYDROGENATION OF ESTERS TO ALCOHOLS AT 25-DEGREES-150-DEGREES [J].
ADKINS, H ;
BILLICA, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (09) :3121-3125
[2]   A CATALYTIC ENANTIOSELECTIVE SYNTHETIC ROUTE TO THE IMPORTANT ANTIDEPRESSANT SERTRALINE [J].
COREY, EJ ;
GANT, TG .
TETRAHEDRON LETTERS, 1994, 35 (30) :5373-5376
[3]   Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].
Davies, HML ;
Bruzinski, PR ;
Lake, DH ;
Kong, N ;
Fall, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907
[4]   ASYMMETRIC-SYNTHESIS OF 1,4-CYCLOHEPTADIENES AND BICYCLO[3.2.1]OCTA-2,6-DIENES BY RHODIUM(II) N-(P-(TERT-BUTYL)PHENYLSULFONYL)PROLINATE CATALYZED-REACTIONS BETWEEN VINYLDIAZOMETHANES AND DIENES [J].
DAVIES, HML ;
PENG, ZQ ;
HOUSER, JH .
TETRAHEDRON LETTERS, 1994, 35 (48) :8939-8942
[5]   Synthesis and evaluation of a novel dirhodium tetraprolinate catalyst containing bridging prolinate ligands [J].
Davies, HML ;
Kong, N .
TETRAHEDRON LETTERS, 1997, 38 (24) :4203-4206
[6]   Rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed asymmetric insertions of vinyl- and phenylcarbenoids into the Si-H bond [J].
Davies, HML ;
Hansen, T ;
Rutberg, J ;
Bruzinski, PR .
TETRAHEDRON LETTERS, 1997, 38 (10) :1741-1744
[7]   Asymmetric synthesis of cyclopentenes by [3+2] annulations between vinylcarbenoids and vinyl ethers [J].
Davies, HML ;
Kong, N ;
Churchill, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6586-6589
[8]   Tandem asymmetric cyclopropanation/cope rearrangement. A highly diastereoselective and enantioselective method for the construction of 1,4-cycloheptadienes [J].
Davies, HML ;
Stafford, DG ;
Doan, BD ;
Houser, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) :3326-3331
[9]   ENANTIOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES BY RHODIUM(II) CATALYZED DECOMPOSITION OF VINYLDIAZOMETHANES IN THE PRESENCE OF ALKENES [J].
DAVIES, HML ;
HUTCHESON, DK .
TETRAHEDRON LETTERS, 1993, 34 (45) :7243-7246
[10]   Asymmetric intermolecular carbenoid C-H insertions catalyzed by rhodium(II) (S)-N-(p-dodecylphenyl)sulfonylprolinate [J].
Davies, HML ;
Hansen, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :9075-9076