Modification of chiral monodentate phosphine (MOP) ligands for palladium-catalyzed asymmetric hydrosilylation of styrenes

被引：26

作者：

Hayashi, T ^{[1
]}

Hirate, S ^{[1
]}

Kitayama, K ^{[1
]}

Tsuji, H ^{[1
]}

Torii, A ^{[1
]}

Uozumi, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

CHEMISTRY LETTERS | 2000年 / 11期

关键词：

D O I：

10.1246/cl.2000.1272

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the palladium-catalyzed asymmetric hydrosilylation of styrene with trichlorosilane, several chiral monophosphine ligands, (R)-2-diarylphosphino-1,1'-binaphthyls (2), were examined for their enantioselectivity. The highest enantioselectivity was observed in the reaction with (R)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino- 1,1'-binaphthyl (2g), which gave (S)-1-phenylethanol of 98% ee after oxidation of the hydrosilylation product.

引用

页码：1272 / 1273

页数：2

共 19 条

[1] 2-Diphenylphosphino-2′-diphenylphosphinyl-1,1′-binaphthalene (BINAPO), an axially chiral heterobidentate ligand for enantioselective catalysis [J].

Gladiali, S ;

Pulacchini, S ;

Fabbri, D ;

Manassero, M ;

Sansoni, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :391-395

[2] ASYMMETRIC HYDROSILYLATION OF OLEFINS CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEX - ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS AND BROMIDES FROM OLEFINS [J].

HAYASHI, T ;

TAMAO, K ;

KATSURO, Y ;

NAKAE, I ;

KUMADA, M .

TETRAHEDRON LETTERS, 1980, 21 (19) :1871-1874

[3]

HAYASHI T, 1999, COMPREHENSIVE ASYMME, V1, pCH7

[4] PALLADIUM-CATALYZED ASYMMETRIC HYDROSILYLATION OF STYRENES WITH A NEW CHIRAL MONODENTATE PHOSPHINE LIGAND [J].

KITAYAMA, K ;

UOZUMI, Y ;

HAYASHI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (15) :1533-1534

[5] STEREOSPECIFIC FUNCTIONALIZATION OF (R)-(-)-1,1'-BI-2-NAPHTHOL TRIFLATE [J].

KURZ, L ;

LEE, G ;

MORGANS, D ;

WALDYKE, MJ ;

WARD, T .

TETRAHEDRON LETTERS, 1990, 31 (44) :6321-6324

[6] PHOSPHETANES AS CHIRAL LIGANDS FOR CATALYTIC ASYMMETRIC REACTIONS - HYDROSILYLATION OF OLEFINS [J].

MARINETTI, A ;

RICARD, L .

ORGANOMETALLICS, 1994, 13 (10) :3956-3962

[7] AN INVESTIGATION INTO A PALLADIUM-CATALYZED HYDROSILYLATION OF OLEFINS [J].

MARINETTI, A .

TETRAHEDRON LETTERS, 1994, 35 (32) :5861-5864

[8]

Nishiyama H, 2000, CATALYTIC ASYMMETRIC, P111

[9] ASYMMETRIC REACTIONS CATALYZED BY CHIRAL METAL-COMPLEXES .40. ASYMMETRIC HYDROSILYLATION OF CYCLOPENTADIENE AND STYRENE WITH CHLOROSILANES CATALYZED BY PALLADIUM COMPLEXES OF CHIRAL (BETA-N-SULFONYLAMINOALKYL)PHOSPHINES [J].

OKADA, T ;

MORIMOTO, T ;

ACHIWA, K .

CHEMISTRY LETTERS, 1990, (06) :999-1002

[10] Highly enantioselective palladium-catalyzed hydrosilylation of norbornene with trichlorosilane using ferrocenyl ligands [J].

Pioda, G ;

Togni, A .

TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3903-3910

← 1 2 →