Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to δ3-amino acids

被引：30

作者：

Aitken, Lewis S. ^{[1
]}

Hammond, Lisa E. ^{[1
]}

Sundaram, Rajkumar ^{[1
]}

Shankland, Kenneth ^{[1
]}

Brown, Geoffrey D. ^{[1
]}

Cobb, Alexander J. A. ^{[1
]}

机构：

[1] Univ Reading, Sch Chem Food & Pharm SCFP, Reading RG6 6AD, Berks, England

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 70期

关键词：

SIMMONS-SMITH CYCLOPROPANATION; ALLYLIC ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; QUATERNARY; GENERATION;

D O I：

10.1039/c5cc05158d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalytic asymmetric synthesis of a novel, highly functionalised cyclopropane system furnished with versatile substituents and containing a quaternary centre is described. The process utilises a new bifunctional catalyst based on the cinchona alkaloid framework and the products made using this catalyst were obtained as single diastereoisomers, with very high enantioselectivities (up to 96% ee). We have also demonstrated that these resulting cyclopropanes are very useful synthetic intermediates to interesting products, such as the difficult to access delta(3)-amino acids.

引用

页码：13558 / 13561

页数：4

共 49 条

[31] Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition [J].

Li, HM ;

Wang, Y ;

Tang, L ;

Wu, FH ;

Liu, XF ;

Guo, CY ;

Foxman, BM ;

Deng, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :105-108

[32] Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes:: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids [J].

Li, HM ;

Wang, Y ;

Tang, L ;

Deng, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9906-9907

[33] Highly enantioselective amination of α-substituted α-cyanoacetates with chiral catalysts accessible from both quinine and quinidine [J].

Liu, XF ;

Li, HM ;

Deng, L .

ORGANIC LETTERS, 2005, 7 (02) :167-169

[34] Catalytic asymmetric Simmons-Smith cyclopropanation of unfunctionalized olefins [J].

Long, J ;

Du, HF ;

Li, K ;

Shi, Y .

TETRAHEDRON LETTERS, 2005, 46 (16) :2737-2740

[35] Asymmetric Simmons-Smith cyclopropanation of unfunctionalized olefins [J].

Long, J ;

Yuan, Y ;

Shi, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13632-13633

[36] Cupreines and cupreidines: An emerging class of bifunctional cinchona organocatalysts [J].

Marcelli, Tommaso ;

van Maarseveen, Jan H. ;

Hiemstra, Henk .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7496-7504

[37] Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes Bearing a Quaternary Stereocenter via Double Michael Reaction Involving Dynamic Kinetic Resolution [J].

Meninno, Sara ;

Croce, Gianluca ;

Lattanzi, Alessandra .

ORGANIC LETTERS, 2013, 15 (13) :3436-3439

[38] Discovery and application of asymmetric reaction by multi-functional thioureas [J].

Miyabe, Hideto ;

Takemoto, Yoshiji .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (07) :785-795

[39] Enantioselective Intramolecular Michael Addition of Nitronates onto Conjugated Esters: Access to Cyclic γ-Amino Acids with up to Three Stereocenters [J].

Nodes, William J. ;

Nutt, David R. ;

Chippindale, Ann M. ;

Cobb, Alexander J. A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) :16016-+

[40] Enantioselective organocatalytic cyclopropanation via ammonium ylides [J].

Papageorgiou, CD ;

de Dios, MAC ;

Ley, SV ;

Gaunt, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) :4641-4644

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