共 35 条
Organocatalyzed Asymmetric Synthesis of Dihydrodibenzofurans Based on a Dienamine Process
被引:30
作者:

Wang, Zi-Yu
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China

Wong, Wing-Tak
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China

Yang, Dan
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
机构:
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
关键词:
DIELS-ALDER REACTION;
ALPHA;
BETA-UNSATURATED ALDEHYDES;
OXIDATIVE CYCLIZATION;
2-ALLYLPHENOLS;
OXYPALLADATION;
CYCLOADDITION;
ANNULATION;
CATALYSIS;
D O I:
10.1021/ol402288y
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The first organocatalyzed asymmetric method for the synthesis of dihydrodibenzofurans based on a dienamine process has been developed. This two-step protocol works with a broad range of substrates and delivers only the cis-diastereomer in good yield with up to 91% ee. The enantioenriched products have been transformed to highly functionalized and partially hydrogenated dibenzofurans in excellent diastereoselectivities.
引用
收藏
页码:4980 / 4983
页数:4
相关论文
共 35 条
[1]
Proline promoted synthesis of ring-fused homodimers:: Self-condensation of α,β-unsaturated aldehydes
[J].
Bench, Bennie J.
;
Liu, Chaomin
;
Evett, Colin R.
;
Watanabe, Coran M. H.
.
JOURNAL OF ORGANIC CHEMISTRY,
2006, 71 (25)
:9458-9463

Bench, Bennie J.
论文数: 0 引用数: 0
h-index: 0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

Liu, Chaomin
论文数: 0 引用数: 0
h-index: 0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

Evett, Colin R.
论文数: 0 引用数: 0
h-index: 0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

Watanabe, Coran M. H.
论文数: 0 引用数: 0
h-index: 0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
[2]
Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
[J].
Bertelsen, Slren
;
Marigo, Mauro
;
Brandes, Sebastian
;
Diner, Peter
;
Jorgensen, Karl Anker
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006, 128 (39)
:12973-12980

Bertelsen, Slren
论文数: 0 引用数: 0
h-index: 0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark

论文数: 引用数:
h-index:
机构:

Brandes, Sebastian
论文数: 0 引用数: 0
h-index: 0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark

Diner, Peter
论文数: 0 引用数: 0
h-index: 0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark

Jorgensen, Karl Anker
论文数: 0 引用数: 0
h-index: 0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
[3]
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
[4]
Total Synthesis of (±)-Galanthamine via a C3-Selective Stille Coupling and IMDA Cycloaddition Cascade of 3,5-Dibromo-2-pyrone
[J].
Chang, Jay Hyok
;
Kang, Ho-Ung
;
Jung, In-Hak
;
Cho, Cheon-Gyu
.
ORGANIC LETTERS,
2010, 12 (09)
:2016-2018

Chang, Jay Hyok
论文数: 0 引用数: 0
h-index: 0
机构:
Hanyang Univ, Dept Chem, Seoul 133791, South Korea Hanyang Univ, Dept Chem, Seoul 133791, South Korea

Kang, Ho-Ung
论文数: 0 引用数: 0
h-index: 0
机构:
Hanyang Univ, Dept Chem, Seoul 133791, South Korea Hanyang Univ, Dept Chem, Seoul 133791, South Korea

Jung, In-Hak
论文数: 0 引用数: 0
h-index: 0
机构:
Hanyang Univ, Dept Chem, Seoul 133791, South Korea Hanyang Univ, Dept Chem, Seoul 133791, South Korea

Cho, Cheon-Gyu
论文数: 0 引用数: 0
h-index: 0
机构:
Hanyang Univ, Dept Chem, Seoul 133791, South Korea Hanyang Univ, Dept Chem, Seoul 133791, South Korea
[5]
Amine-catalyzed cyclizations of tethered α,β-unsaturated carbonyl compounds
[J].
de Figueiredo, Renata Marcia
;
Froehlich, Roland
;
Christmann, Mathias
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2008, 47 (08)
:1450-1453

de Figueiredo, Renata Marcia
论文数: 0 引用数: 0
h-index: 0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

Froehlich, Roland
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Munster, Inst Organ Chem, D-4400 Munster, Germany Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

Christmann, Mathias
论文数: 0 引用数: 0
h-index: 0
机构:
Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[6]
Novel generation of an o-quinone methide from 2-(2′-cyclohexenyl)phenol by excited state intramolecular proton transfer and subsequent C-C fragmentation
[J].
Delgado, J
;
Espinós, A
;
Jiménez, MC
;
Miranda, MA
.
CHEMICAL COMMUNICATIONS,
2002, (22)
:2636-2637

Delgado, J
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain

Espinós, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain

Jiménez, MC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain

Miranda, MA
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Dept Quim, Valencia 46071, Spain
[7]
Stability relationships in bicyclic ketones
[J].
Gordon, HL
;
Freeman, S
;
Hudlicky, T
.
SYNLETT,
2005, (19)
:2911-2914

Gordon, HL
论文数: 0 引用数: 0
h-index: 0
机构:
Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

Freeman, S
论文数: 0 引用数: 0
h-index: 0
机构: Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

论文数: 引用数:
h-index:
机构:
[8]
Hypophosphite mediated carbon-carbon bond formation: a clean approach to radical methodology
[J].
Graham, SR
;
Murphy, JA
;
Coates, D
.
TETRAHEDRON LETTERS,
1999, 40 (12)
:2415-2416

Graham, SR
论文数: 0 引用数: 0
h-index: 0
机构: Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland

Murphy, JA
论文数: 0 引用数: 0
h-index: 0
机构: Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland

Coates, D
论文数: 0 引用数: 0
h-index: 0
机构: Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
[9]
Iridium(III)-catalyzed tandem Claisen rearrangement-intramolecular hydroaryloxylation of aryl allyl ethers to form dihydrobenzofurans
[J].
Grant, VH
;
Liu, B
.
TETRAHEDRON LETTERS,
2005, 46 (08)
:1237-1239

Grant, VH
论文数: 0 引用数: 0
h-index: 0
机构:
GlaxoSmithKlin, Chem Dev, Res Triangle Pk, NC 27709 USA GlaxoSmithKlin, Chem Dev, Res Triangle Pk, NC 27709 USA

Liu, B
论文数: 0 引用数: 0
h-index: 0
机构:
GlaxoSmithKlin, Chem Dev, Res Triangle Pk, NC 27709 USA GlaxoSmithKlin, Chem Dev, Res Triangle Pk, NC 27709 USA
[10]
Lewis Acid Catalyzed Intramolecular Direct Ene Reaction of Indoles
[J].
Han, Bo
;
Xiao, You-Cai
;
Yao, Yuan
;
Chen, Ying-Chun
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2010, 49 (52)
:10189-10191

Han, Bo
论文数: 0 引用数: 0
h-index: 0
机构:
Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China

Xiao, You-Cai
论文数: 0 引用数: 0
h-index: 0
机构:
Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China

Yao, Yuan
论文数: 0 引用数: 0
h-index: 0
机构:
Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China

Chen, Ying-Chun
论文数: 0 引用数: 0
h-index: 0
机构:
Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China
Sichuan Univ, State Key Lab Biotherapy, W China Hosp, Chengdu 610041, Peoples R China Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China