Organocatalytic one-pot asymmetric synthesis of functionalized tricyclic carbon frameworks from a triple-cascade/Diels-Alder sequence

被引：243

作者：

Enders, Dieter ^{[1
]}

Huettl, Matthias R. M. ^{[1
]}

Runsink, Jan ^{[1
]}

Raabe, Gerhard ^{[1
]}

Wendt, Bianca ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 03期

关键词：

asymmetric synthesis; cycloaddition; domino reactions; multicomponent reactions; organocatalysis;

D O I：

10.1002/anie.200603434

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Hitting the teens! Five C-C bonds and eight stereocenters were formed in a one-pot asymmetric multicomponent domino reaction, which led to the functionalized tricyclic diterpenoid-type core structures (see scheme, IMDA = intramolecular Diels-Alder reaction). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：467 / 469

页数：3

共 52 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2]

[Anonymous], 1991, Comprehensive Organic Synthesis

[3]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[4] THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

BRIEGER, G ;

BENNETT, JN .

CHEMICAL REVIEWS, 1980, 80 (01) :63-97

[5] A proline-catalyzed asymmetric Robinson annulation reaction [J].

Bui, T ;

Barbas, CF .

TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954

[6]

Corey E.J., 2002, ANGEW CHEM, V114, P1724, DOI DOI 10.1021/JACS.7B06567

[7]

Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO

[8]

2-B

[9] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

CRAIG, D .

CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238

[10]

Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650

← 1 2 3 4 5 6 →