共 65 条
A highly enantioselective Hg(II)-catalyzed Sakurai-Hosomi reaction of isatins with allyltrimethylsilanes
被引:35
作者:

Cao, Zhong-Yan
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机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China

Jiang, Jia-Sheng
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h-index: 0
机构:
Mengcheng 1 Middle Sch, Bozhou 233500, Anhui, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China

Zhou, Jian
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机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
机构:
[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
[2] Mengcheng 1 Middle Sch, Bozhou 233500, Anhui, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词:
CATALYZED ASYMMETRIC ALLYLATION;
VINYLOGOUS ALDOL REACTION;
SPIROCYCLIC OXINDOLES;
CARBONYL-COMPOUNDS;
ACID;
IMINES;
HG(CLO4)(2)CENTER-DOT-3H(2)O;
3-HYDROXYOXINDOLES;
CYCLOPROPANATION;
DIAZOOXINDOLES;
D O I:
10.1039/c5ob02582f
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A chiral complex derived from (S)-difluorophos and Hg(OTf)(2) is identified as a powerful catalyst for the Sakurai-Hosomi reaction of isatins with allyltrimethylsilane, allowing the facile synthesis of valuable building blocks 3-allyl-3-hydroxyoxindoles in up to 97% ee, with only 0.5-1.0 mol% of catalyst loading.
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收藏
页码:5500 / 5504
页数:5
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共 65 条
[1]
Palladium-Catalyzed Enantioselective Ene and Aldol Reactions with Isatins, Keto Esters, and Diketones: Reliable Approach to Chiral Tertiary Alcohols
[J].
Aikawa, Kohsuke
;
Mimura, Shunsuke
;
Numata, Yukinobu
;
Mikami, Koichi
.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2011, 2011 (01)
:62-65

Aikawa, Kohsuke
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

Mimura, Shunsuke
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

Numata, Yukinobu
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

Mikami, Koichi
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
[2]
Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences
[J].
Alcaide, B
;
Almendros, P
;
Rodríguez-Acebes, R
.
JOURNAL OF ORGANIC CHEMISTRY,
2006, 71 (06)
:2346-2351

Alcaide, B
论文数: 0 引用数: 0
h-index: 0
机构: CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

Almendros, P
论文数: 0 引用数: 0
h-index: 0
机构: CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

Rodríguez-Acebes, R
论文数: 0 引用数: 0
h-index: 0
机构: CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[3]
An Alternative to Precious Metals: Hg(ClO4)2•3H2O as a Cheap and Water-Tolerant Catalyst for the Cycloisomerization of Allenols
[J].
Alcaide, Benito
;
Almendros, Pedro
;
Luna, Amparo
;
Soriano, Elena
.
JOURNAL OF ORGANIC CHEMISTRY,
2015, 80 (14)
:7050-7057

Alcaide, Benito
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain

Almendros, Pedro
论文数: 0 引用数: 0
h-index: 0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain

Luna, Amparo
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain

Soriano, Elena
论文数: 0 引用数: 0
h-index: 0
机构:
CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain
[4]
Highly Stereoselective Olefin Cyclopropanation of Diazooxindoles Catalyzed by a C2-Symmetric Spiroketal Bisphosphine/Au(I) Complex
[J].
Cao, Zhong-Yan
;
Wang, Xiaoming
;
Tan, Chen
;
Zhao, Xiao-Li
;
Zhou, Jian
;
Ding, Kuiling
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2013, 135 (22)
:8197-8200

Cao, Zhong-Yan
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Wang, Xiaoming
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Tan, Chen
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Zhao, Xiao-Li
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Zhou, Jian
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Ding, Kuiling
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[5]
A Highly Diastereo- and Enantioselective Hg(II)-Catalyzed Cyclopropanation of Diazooxindoles and Alkenes
[J].
Cao, Zhong-Yan
;
Zhou, Feng
;
Yu, Yi-Hua
;
Zhou, Jian
.
ORGANIC LETTERS,
2013, 15 (01)
:42-45

Cao, Zhong-Yan
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Zhou, Feng
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Yu, Yi-Hua
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Dept Phys, Shanghai Key Lab Magnet Resonance, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Zhou, Jian
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[6]
A Hg(ClO4)2•3H2O Catalyzed Sakurai-Hosomi Allylation of Isatins and Isatin Ketoimines Using Allyltrimethylsilane
[J].
Cao, Zhong-Yan
;
Zhang, Yan
;
Ji, Cong-Bin
;
Zhou, Jian
.
ORGANIC LETTERS,
2011, 13 (24)
:6398-6401

Cao, Zhong-Yan
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Zhang, Yan
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Ji, Cong-Bin
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

Zhou, Jian
论文数: 0 引用数: 0
h-index: 0
机构:
E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[7]
Direct Catalytic Enantioselective Vinylogous Aldol Reaction of α-Branched Enals with Isatins
[J].
Cassani, Carlo
;
Melchiorre, Paolo
.
ORGANIC LETTERS,
2012, 14 (21)
:5590-5593

Cassani, Carlo
论文数: 0 引用数: 0
h-index: 0
机构:
ICIQ Inst Chem Res Catalonia, Tarragona 43007, Spain ICREA, Barcelona 08010, Spain

Melchiorre, Paolo
论文数: 0 引用数: 0
h-index: 0
机构:
ICREA, Barcelona 08010, Spain
ICIQ Inst Chem Res Catalonia, Tarragona 43007, Spain ICREA, Barcelona 08010, Spain
[8]
The toxicology of mercury and its chemical compounds
[J].
Clarkson, Thomas W.
;
Magos, Laszlo
.
CRITICAL REVIEWS IN TOXICOLOGY,
2006, 36 (08)
:609-662

Clarkson, Thomas W.
论文数: 0 引用数: 0
h-index: 0
机构: Univ Rochester, Sch Med, Dept Environm Med, Rochester, NY USA

Magos, Laszlo
论文数: 0 引用数: 0
h-index: 0
机构: Univ Rochester, Sch Med, Dept Environm Med, Rochester, NY USA
[9]
The chemistry of isatins: a review from 1975 to 1999
[J].
da Silva, JFM
;
Garden, SJ
;
Pinto, AC
.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY,
2001, 12 (03)
:273-324

da Silva, JFM
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil

Garden, SJ
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil

Pinto, AC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil
[10]
Stereoselective Synthesis of 1-Methyl-3′,4′,5′,6′-tetrahydrospiro[indoline-3,2′-pyran]-2-one Derivatives via Prins Cyclization
[J].
Damera, Krishna
;
Yu, Bingchen
;
Wang, Binghe
.
JOURNAL OF ORGANIC CHEMISTRY,
2015, 80 (11)
:5457-5463

Damera, Krishna
论文数: 0 引用数: 0
h-index: 0
机构:
Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

Yu, Bingchen
论文数: 0 引用数: 0
h-index: 0
机构: Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

Wang, Binghe
论文数: 0 引用数: 0
h-index: 0
机构: Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA