Synergistic Catalysis for the Asymmetric [3+2] Cycloaddition of Vinyl Aziridines with α,β-Unsaturated Aldehydes

被引：39

作者：

Naesborg, Line ^{[1
]}

Tur, Fernando ^{[1
]}

Meazza, Marta ^{[1
]}

Blom, Jakob ^{[1
]}

Halskov, Kim Soholm ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Langelandsgade 140, DK-8000 Aarhus C, Denmark

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 02期

关键词：

organocatalysis; synergistic catalysis; synthetic methods; transition-metal catalysis; vinyl aziridines; INFLUENZA NEURAMINIDASE INHIBITORS; DYNAMIC KINETIC RESOLUTION; TRANSITION-METAL CATALYSIS; NITROGEN-HETEROCYCLES; ALPHA-ALLYLATION; ENANTIOSELECTIVE SYNTHESIS; ENAMINE CATALYSIS; AMINE CATALYSIS; DRUG DISCOVERY; RING;

D O I：

10.1002/chem.201604995

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric [3+2] cycloaddition of vinyl aziridines with alpha,beta-unsaturated aldehydes, based on synergistic catalysis, is disclosed. This methodology allows the formation of attractive pyrrolidine structures in good yields (up to 84%), moderate diastereoselectivity, and high enantioselectivity values (up to >99% ee). Additionally, a tricyclic pyrrolidine core structure found in biologically active molecules was synthesized in a one-pot fashion by using the presented reaction concept. Finally, a mechanistic proposal is outlined.

引用

页码：268 / 272

页数：5

共 78 条

[1] Two-and Three-dimensional Rings in Drugs [J].

Aldeghi, Matteo ;

Malhotra, Shipra ;

Selwood, David L. ;

Chan, Ah Wing Edith .

CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 83 (04) :450-461

[2] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[3] Palladium-catalyzed aminoallylation of activated olefins with allylic halides and phthalimide [J].

Aoyagi, K ;

Nakamura, H ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :5977-5980

[4] Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition [J].

Arena, Giada ;

Chen, C. Chun ;

Leonori, Daniele ;

Aggarwal, Varinder K. .

ORGANIC LETTERS, 2013, 15 (16) :4250-4253

[5] Design, synthesis, and biological evaluation of conformationally restricted rivastigmine analogues [J].

Bolognesi, ML ;

Bartolini, M ;

Cavalli, A ;

Andrisano, V ;

Rosini, M ;

Minarini, A ;

Melchiorre, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5945-5952

[6]

Brazier J. B., 2009, ASYMMETRIC ORGANOCAT, P281

[7]

Bur-khard J. A., 2010, ANGEW CHEM, V122, P9236

[8] Oxetanes as Versatile Elements in Drug Discovery and Synthesis [J].

Burkhard, Johannes A. ;

Wuitschik, Georg ;

Rogers-Evans, Mark ;

Mueller, Klaus ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) :9052-9067

[9] Room temperature ring-opening cyclization reactions of 2-vinylaziridines with isocyanates, carbodiimides, and isothiocyanates catalyzed by [Pd(OAc)2]/PPh3 [J].

Butler, DCD ;

Inman, GA ;

Alper, H .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5887-5890

[10] Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five-Membered Heterocycles [J].

Cardoso, Ana L. ;

Pinho e Melo, Teresa M. V. D. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (33) :6479-6501

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