Highly Efficient Hydrogen-Bonding Catalysis of the Diels-Alder Reaction of 3-Vinylindoles and Methyleneindolinones Provides Carbazolespirooxindole Skeletons

被引：336

作者：

Tan, Bin ^{[1
,2
,3
]}

Hernandez-Torres, Gloria ^{[1
,2
,3
,4
]}

Barbas, Carlos F., III ^{[1
,2
,3
]}

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

[4] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 32期

关键词：

ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC ORGANOCATALYSIS; STEREOSELECTIVE-SYNTHESIS; SPIROCYCLIC OXINDOLES; NONCOVALENT CATALYSIS; CONJUGATE ADDITION; DOMINO REACTIONS; MICHAEL REACTION;

D O I：

10.1021/ja203812h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Carbazolespirooxindole derivatives were synthesized in a high-yielding, atypically rapid, stereocontrolled Diels-Alder reaction catalyzed by a C-2-symmetric bisthiourea organocatalyst. Simple precursors and mild conditions were used to construct carbazolespirooxindole derivatives with high enantiopurity and structural diversity under H-bonding catalysis. The practical approach recycles the organocatalyst and solvent. This simple and efficient operational procedure will allow diversity-oriented syntheses of this intriguing class of compounds.

引用

页码：12354 / 12357

页数：4

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