First asymmetric intermolecular bromoesterification catalyzed by chiral Bronsted acid

被引：47

作者：

Li, Guang-xun ^{[1
,2
]}

Fu, Qing-quan ^{[2
]}

Zhang, Xiao-mei ^{[1
]}

Jiang, Jun ^{[3
]}

Tang, Zhuo ^{[2
]}

机构：

[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chiraltechnol Sichuan Pr, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China

[3] Wenzhou Univ, Coll Chem & Mat Engn, Wenzou 325027, Zhejiang Provin, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 3-4期

关键词：

ENANTIOSELECTIVE IODOLACTONIZATION; MOLECULAR RECOGNITION; BROMOLACTONIZATION; HALOCYCLIZATION; DERIVATIVES; COMPLEXES; OLEFINS; DESIGN;

D O I：

10.1016/j.tetasy.2012.02.016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first successful enantioselective intermolecular bromoesterification was realized by using a chiral phosphoric acid as a catalyst. The reaction was optimized after screening 2-aminopyridine based basic catalysts. cinchona alkaloid based basic catalysts, and binol backbone based Bronsted acid catalysts. Up to 70% ee and a moderate yield were achieved under the optimized condition. An ion-pair mechanism has been suggested in order to explain the reaction results. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：245 / 251

页数：7

共 40 条

[11] Synthesis of a trans-fused perhydroindan analog of hispidospermidin
Ellis, DA
Hart, DJ
Zhao, L
[J]. TETRAHEDRON LETTERS, 2000, 41 (49) : 9357 - 9360
[12] MOLECULAR RECOGNITION - A REMARKABLY SIMPLE RECEPTOR FOR THE SELECTIVE COMPLEXATION OF DICARBOXYLIC-ACIDS
GARCIATELLADO, F
GOSWAMI, S
CHANG, SK
GEIB, SJ
HAMILTON, AD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) : 7393 - 7394
[13] An approach to enantioselective 5-endo halo-lactonization reactions
Garnier, Jean Marc
Robin, Sylvie
Rousseau, Gerard
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (20) : 3281 - 3291
[14] Asymmetric organocatalytic biginelli reactions:: A new approach to quickly access optically active 3,4-Dihydropyrimidin-2-(1H)-ones
Gong, Liu-Zhu
Chen, Xiao-Hua
Xu, Xiao-Ying
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (32) : 8920 - 8926
[15] The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion
Grossman, RB
Trupp, RJ
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1998, 76 (09) : 1233 - 1237
[16] Iodine monochloride-amine complexes: An experimental and computational approach to new chiral electrophiles
Haas, J
Bissmire, S
Wirth, T
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) : 5777 - 5785
[17] Reagent-controlled stereoselective iodolactonizations
Haas, J
Piguel, S
Wirth, T
[J]. ORGANIC LETTERS, 2002, 4 (02) : 297 - 300
[18] Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions
Hennecke, Ulrich
Mueller, Christian H.
Froehlich, Roland
[J]. ORGANIC LETTERS, 2011, 13 (05) : 860 - 863
[19] Enantioselective Bromocyclization of Olefins Catalyzed by Chiral Phosphoric Acid
Huang, Deshun
Wang, Haining
Xue, Fazhen
Guan, Huan
Li, Lijun
Peng, Xianyou
Shi, Yian
[J]. ORGANIC LETTERS, 2011, 13 (24) : 6350 - 6353
[20] First total synthesis of natural 6-epiplakortolide E
Jung, M
Ham, J
Song, J
[J]. ORGANIC LETTERS, 2002, 4 (16) : 2763 - 2765

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