Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization

被引：144

作者：

Belot, Sebastien ^{[2
]}

Vogt, Kim A. ^{[1
]}

Besnard, Celine ^{[3
]}

Krause, Norbert ^{[1
]}

Alexakis, Alexandre ^{[2
]}

机构：

[1] Tech Univ Dortmund, D-44227 Dortmund, Germany

[2] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland

[3] Univ Geneva, Lab Cristallog, CH-1211 Geneva 4, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 47期

关键词：

cyclization; gold; heterocycles; Michael addition; organocatalysis; GOLD CATALYSIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; ALDEHYDES; ALKYNES; CYCLOISOMERIZATION; NITROALKENES; ACTIVATION; DIVERSITY;

D O I：

10.1002/anie.200903905

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Au-rganocatalytic reaction: A one-pot process consisting of a Michael addition to a nitroenyne and a subsequent acetalization/ cyclization is reported (see scheme; TMS=trimethylsilyl), which results in the formation of nitro-substituted tetrahydrofuranyl ethers with high diastereo- and enantioselectivities. Organocatalysis and gold catalysis are compatible and complementary in a one-pot process © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8923 / 8926

页数：4

共 38 条

[1] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[2] Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin [J].

Andrey, O ;

Vidonne, A ;

Alexakis, A .

TETRAHEDRON LETTERS, 2003, 44 (43) :7901-7904

[3]

[Anonymous], 2007, CHEM REV, V107, P5413

[4] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[5] An asymmetric synthesis of the novel H3 agonist (+)-(3R,4R)-3-(4-imidazolyl)-4-methylpyrrolidine dihydrochloride (Sch 50971) [J].

Aslanian, R ;

Lee, G ;

Iyer, RV ;

Shih, NY ;

Piwinski, JJ ;

Draper, RW ;

McPhail, AT .

TETRAHEDRON-ASYMMETRY, 2000, 11 (19) :3867-3871

[6] Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Nitrodienes [J].

Belot, Sebastien ;

Massaro, Assunta ;

Tenti, Alice ;

Mordini, Alessandro ;

Alexakis, Alexandre .

ORGANIC LETTERS, 2008, 10 (20) :4557-4560

[7] Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols [J].

Belting, Volker ;

Krause, Norbert .

ORGANIC LETTERS, 2006, 8 (20) :4489-4492

[8] Gold-catalyzed cycloisomerization of alk-4-yn-1-ones [J].

Belting, Volker ;

Krause, Norbert .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (06) :1221-1225

[9] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Tanaka, F ;

Barbas, CF .

SYNTHESIS-STUTTGART, 2004, (09) :1509-1521

[10] Direct carbocyclization of aldehydes with alkynes: Combining gold catalysis with aminocatalysis [J].

Binder, Jorg T. ;

Crone, Benedikt ;

Haug, Timm T. ;

Menz, Helge ;

Kirsch, Stefan F. .

ORGANIC LETTERS, 2008, 10 (05) :1025-1028

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