About the crystal structure of [Rh((S,S)-DIPAMP)((Z)-2-benzoylamino-3-(3,4-dimethoxyphenyl)-methyl acrylate)]BF4:: Major or minor catalyst-substrate complex?

被引：32

作者：

Schmidt, T

Baumann, W

Drexler, HJ

Arrieta, A

Heller, D

Buschmann, H

机构：

[1] Univ Rostock EV, Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany

[2] ESTEVE, ES-08041 Barcelona, Spain

来源：

ORGANOMETALLICS | 2005年 / 24卷 / 16期

关键词：

D O I：

10.1021/om0490536

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric hydrogenation of (Z)-2-benzoylamino-3-(3,4-dimethoxyphenyl)-methyl acrylate with [Rh((S,S)-DIPAMP)(MeOH)(2)]BF4 was investigated. Low temperature NMR measurements prove the recently published X-ray structure of [Rh((S,S)-DIPAMP)((Z)-2-benzoylamino-3-(3,4-dimethoxyphenyl)-methyl acrylate)]BF4 to be the major substrate complex. The asymmetric hydrogenation of the prochiral DOPA precursor with the cationic Rh-DIPAMP catalyst therefore follows the "anti-lock-and-key" motif analogue to similar substrate complexes already known from literature.

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页码：3842 / 3848

页数：7

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共 45 条

[11] IDENTIFICATION OF THE ENANTIOSELECTIVE STEP IN THE ASYMMETRIC CATALYTIC-HYDROGENATION OF A PROCHIRAL OLEFIN [J].

CHAN, ASC ;

PLUTH, JJ ;

HALPERN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5952-5954

[12] THE ORIGINS OF THE ENANTIOSELECTION IN ASYMMETRIC CATALYTIC-HYDROGENATION OF AMINO-ACID PRECURSORS [J].

CHUA, PS ;

ROBERTS, NK ;

BOSNICH, B ;

OKRASINSKI, SJ ;

HALPERN, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (24) :1278-1280

[13] Are β-acylaminoacrylates hydrogenated in the same way as α-acylaminoacrylates? [J].

Drexler, HJ ;

Baumann, W ;

Schmidt, T ;

Zhang, SL ;

Sun, AL ;

Spannenberg, A ;

Fischer, C ;

Buschmann, H ;

Heller, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (08) :1184-1188

[14] Cationic Rh-bisphosphine-diolefin complexes as precatalysts for enantioselective catalysis - what information do single crystal structures contain regarding product chirality? [J].

Drexler, HJ ;

Zhang, SL ;

Sun, AL ;

Spannenberg, A ;

Arrieta, A ;

Preetz, A ;

Heller, D .

TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2139-2150

[15] Part III. COD versus NBD precatalysts. Dramatic difference in the asymmetric hydrogenation of prochiral olefins with five-membered diphosphine Rh-hydrogenation catalysts [J].

Drexler, HJ ;

Baumann, W ;

Spannenberg, A ;

Fischer, C ;

Heller, D .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :89-102

[16] Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes [J].

Evans, DA ;

Michael, FE ;

Tedrow, JS ;

Campos, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3534-3543

[17] Large-scale computational modeling of [Rh(DuPHOS)]+-catalyzed hydrogenation of prochiral enamides:: Reaction pathways and the origin of enantioselection [J].

Feldgus, S ;

Landis, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12714-12727

[18] MOLECULAR MECHANICS AND NOE INVESTIGATIONS OF THE SOLUTION STRUCTURES OF INTERMEDIATES IN THE [RH(CHIRAL BISPHOSPHINE)]+-CATALYZED HYDROGENATION OF PROCHIRAL ENAMIDES [J].

GIOVANNETTI, JS ;

KELLY, CM ;

LANDIS, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4040-4057

[19] Mechanism of asymmetric hydrogenation catalyzed by a rhodium complex of (S,S)-1,2-bis(tert-butylmethylphosphino)ethane.: Dihydride mechanism of asymmetric hydrogenation [J].

Gridnev, ID ;

Higashi, N ;

Asakura, K ;

Imamoto, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7183-7194

[20] On the mechanism of stereoselection in Rh-catalyzed asymmetric hydrogenation: A general approach for predicting the sense of enantioselectivity [J].

Gridnev, ID ;

Imamoto, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (09) :633-644

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