共 39 条
Synthesis and application of bulky phosphoramidites: highly effective monophosphorus ligands for asymmetric hydrosilylation of styrenes
被引:24
作者:

Zhang, Feng
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

Fan, Qing-Hua
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
机构:
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
基金:
中国国家自然科学基金;
关键词:
PALLADIUM-CATALYZED HYDROSILYLATION;
MONODENTATE PHOSPHORUS LIGANDS;
ENANTIOSELECTIVE HYDROGENATION;
PHOSPHINE LIGAND;
COMPLEXES;
OLEFINS;
MOP;
D O I:
10.1039/b909334f
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A series of bulky monodentate phosphoramidite ligands were synthesized from chiral 3,3'-diaryl substituted BINOL derivatives and achiral or dendritic amines in good yields. Asymmetric hydrosilylation of styrenes with trichlorosilane in the presence of palladium complexes of these bulky ligands gave chiral silanes in high yields with excellent activity and productivity. Oxidation of these chiral silanes with hydrogen peroxide gave the corresponding chiral secondary alcohols in up to 96% ee.
引用
收藏
页码:4470 / 4474
页数:5
相关论文
共 39 条
[1]
Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects
[J].
Arnold, LA
;
Imbos, R
;
Mandoli, A
;
de Vries, AHM
;
Naasz, R
;
Feringa, BL
.
TETRAHEDRON,
2000, 56 (18)
:2865-2878

Arnold, LA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

Imbos, R
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

Mandoli, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

de Vries, AHM
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

Naasz, R
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

Feringa, BL
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
[2]
The combinatorial approach to asymmetric hydrogenation: Phosphoramidite libraries, ruthenacycles, and artificial enzymes
[J].
de Vries, Johannes G.
;
Lefort, Laurent
.
CHEMISTRY-A EUROPEAN JOURNAL,
2006, 12 (18)
:4722-4734

de Vries, Johannes G.
论文数: 0 引用数: 0
h-index: 0
机构:
DSM Res BV, Life Sci Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands DSM Res BV, Life Sci Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

Lefort, Laurent
论文数: 0 引用数: 0
h-index: 0
机构:
DSM Res BV, Life Sci Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands DSM Res BV, Life Sci Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands
[3]
BINOL-derived phosphoramidites in asymmetric hydrogenation: can the presence of a functionality in the amino group influence the catalytic outcome?
[J].
Eberhardt, Luc
;
Armspach, Dominique
;
Harrowfield, Jack
;
Matt, Dominique
.
CHEMICAL SOCIETY REVIEWS,
2008, 37 (04)
:839-864

Eberhardt, Luc
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Strasbourg, CNRS, UMR 7177, Inst Chim,Lab Chim Inorgan Mol, F-67008 Strasbourg, France Univ Strasbourg, CNRS, UMR 7177, Inst Chim,Lab Chim Inorgan Mol, F-67008 Strasbourg, France

论文数: 引用数:
h-index:
机构:

Harrowfield, Jack
论文数: 0 引用数: 0
h-index: 0
机构:
ULP, CNRS, UMR 7006, ISIS, F-67083 Strasbourg, France Univ Strasbourg, CNRS, UMR 7177, Inst Chim,Lab Chim Inorgan Mol, F-67008 Strasbourg, France

论文数: 引用数:
h-index:
机构:
[4]
High enantioselectivity is induced by a single monodentate phosphoramidite ligand in iridium-catalyzed asymmetric hydrogenation
[J].
Giacomina, Francesca
;
Meetsma, Auke
;
Panella, Lavinia
;
Lefort, Laurent
;
de Vries, Andre H. M.
;
de Vries, Johannes G.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2007, 46 (09)
:1497-1500

Giacomina, Francesca
论文数: 0 引用数: 0
h-index: 0
机构: DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

Meetsma, Auke
论文数: 0 引用数: 0
h-index: 0
机构: DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

Panella, Lavinia
论文数: 0 引用数: 0
h-index: 0
机构: DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

Lefort, Laurent
论文数: 0 引用数: 0
h-index: 0
机构: DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

de Vries, Andre H. M.
论文数: 0 引用数: 0
h-index: 0
机构: DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

de Vries, Johannes G.
论文数: 0 引用数: 0
h-index: 0
机构: DSM Pharmaceut Prod, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands
[5]
The role of secondary interactions in the asymmetric palladium-catalysed hydrosilylation of olefins with monophosphane ligands
[J].
Gibson, Susan E.
;
Rudd, Matthew
.
ADVANCED SYNTHESIS & CATALYSIS,
2007, 349 (06)
:781-795

Gibson, Susan E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

Rudd, Matthew
论文数: 0 引用数: 0
h-index: 0
机构:
Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[6]
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

Gladiali, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

Pulacchini, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

Fabbri, D
论文数: 0 引用数: 0
h-index: 0
机构: Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

Manassero, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

Sansoni, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
[7]
Asymmetric palladium-catalyzed hydrosilylation of styrenes using efficient chiral spiro phosphoramidite ligands
[J].
Guo, XX
;
Xie, JH
;
Hou, GH
;
Shi, WH
;
Wang, LX
;
Zhou, QL
.
TETRAHEDRON-ASYMMETRY,
2004, 15 (14)
:2231-2234

Guo, XX
论文数: 0 引用数: 0
h-index: 0
机构: E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

Xie, JH
论文数: 0 引用数: 0
h-index: 0
机构: E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

Hou, GH
论文数: 0 引用数: 0
h-index: 0
机构: E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

Shi, WH
论文数: 0 引用数: 0
h-index: 0
机构: E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

Wang, LX
论文数: 0 引用数: 0
h-index: 0
机构: E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

Zhou, QL
论文数: 0 引用数: 0
h-index: 0
机构:
E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[8]
Palladium-catalyzed asymmetric hydrosilylation of 4-substituted 1-buten-3-ynes. Catalytic asymmetric synthesis of axially chiral allenylsilanes
[J].
Han, JW
;
Tokunaga, N
;
Hayashi, T
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001, 123 (51)
:12915-12916

Han, JW
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

Tokunaga, N
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

Hayashi, T
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
[9]
Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies
[J].
Hayashi, T
;
Hirate, S
;
Kitayama, K
;
Tsuji, H
;
Torii, A
;
Uozumi, Y
.
JOURNAL OF ORGANIC CHEMISTRY,
2001, 66 (04)
:1441-1449

Hayashi, T
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

Hirate, S
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

Kitayama, K
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

Tsuji, H
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

Torii, A
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

Uozumi, Y
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
[10]
Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions
[J].
Hayashi, T
.
ACCOUNTS OF CHEMICAL RESEARCH,
2000, 33 (06)
:354-362

Hayashi, T
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan