Highly enantioselective palladium-catalyzed hydrosilylation of norbornene with trichlorosilane using ferrocenyl ligands

被引：58

作者：

Pioda, G ^{[1
]}

Togni, A ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, ETH Zentrum, Inorgan Chem Lab, CH-8092 Zurich, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(98)00409-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Pd-catalyzed hydrosilylation of norbornene with trichlorosilane using different chiral ferrocenyl ligands containing a phosphine and a pyrazole as donors was studied. Both steric and electronic factors affect stereoselectivity in this system. The combination of a sterically bulky pyrazole substituent with a pi-acidic phosphine leads to an enantioselectivity of >99.5% ee. Important substrate electronic effects on stereoselectivity were observed using para-substituted styrenes. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3903 / 3910

页数：8

共 23 条

[11] ASYMMETRIC HYDROSILYLATION OF OLEFINS CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEX - ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS AND BROMIDES FROM OLEFINS
HAYASHI, T
TAMAO, K
KATSURO, Y
NAKAE, I
KUMADA, M
[J]. TETRAHEDRON LETTERS, 1980, 21 (19) : 1871 - 1874
[12] OKAMOTO Y, 1958, J AM CHEM SOC, V80, P4079
[13] Theoretical study of platinum(0)-catalyzed hydrosilylation of ethylene. Chalk-Harrod mechanism or modified Chalk-Harrod mechanism
Sakaki, S
Mizoe, N
Sugimoto, M
[J]. ORGANOMETALLICS, 1998, 17 (12) : 2510 - 2523
[14] THE SELECTIVITY RELATIONSHIP - AN EXAMINATION OF THE ELECTROPHILIC SUBSTITUTION, ELECTROPHILIC SIDE-CHAIN AND HAMMETT SIDE-CHAIN REACTIONS OF TOLUENE AND TOLYL DERIVATIVES
STOCK, LM
BROWN, HC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (13) : 3323 - 3329
[15] SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .20. HYDROGEN-PEROXIDE OXIDATION OF THE SILICON-CARBON BOND IN ORGANOALKOXYSILANES
TAMAO, K
ISHIDA, N
TANAKA, T
KUMADA, M
[J]. ORGANOMETALLICS, 1983, 2 (11) : 1694 - 1696
[16] SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .35. SILAFUNCTIONAL ALPHA,BETA-EPOXY SILANES - TRANSFORMATION INTO ERYTHRO AND THREO 1,2-DIOL SKELETONS AND ITS APPLICATION TO THE SYNTHESIS OF (+/-)-EXO-BREVICOMIN
TAMAO, K
NAKAJO, E
ITO, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) : 4412 - 4414
[17] Togni A, 1998, METALLOCENES: SYNTHESIS - REACTIVITY - APPLICATIONS, VOLS 1 AND 2, P685, DOI 10.1002/9783527619542.ch11
[18] Palladium-catalyzed asymmetric allylic amination using ferrocenyl pyrazole ligands: Steric control of eta(3)-allyl configuration and site-selective nucleophilic attack
Togni, A
Burckhardt, U
Gramlich, V
Pregosin, PS
Salzmann, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) : 1031 - 1037
[19] A NOVEL EASILY ACCESSIBLE CHIRAL FERROCENYLDIPHOSPHINE FOR HIGHLY ENANTIOSELECTIVE HYDROGENATION, ALLYLIC ALKYLATION, AND HYDROBORATION REACTIONS
TOGNI, A
BREUTEL, C
SCHNYDER, A
SPINDLER, F
LANDERT, H
TIJANI, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) : 4062 - 4066
[20] ASYMMETRIC HYDROSILYLATION OF 1-ALKENES CATALYZED BY PALLADIUM-MOP
UOZUMI, Y
KITAYAMA, K
HAYASHI, T
YANAGI, K
FUKUYO, E
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (03) : 713 - 722

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