Cu(I)-Catalyzed Highly Enantioselective [3+3] Cycloaddition between Two Different 1,3-Dipoles, Phthalazinium Dicyanomethanides and Iminoester-Derived Azomethine Ylides

被引：49

作者：

Yuan, Chunhao ^{[1
]}

Liu, Honglei ^{[1
]}

Gao, Zhenzhen ^{[1
]}

Zhou, Leijie ^{[1
]}

Feng, Yalin ^{[1
]}

Xiao, Yumei ^{[1
]}

Guo, Hongchao ^{[1
]}

机构：

[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 01期

关键词：

PHOSPHINE-CATALYZED 3+2; NATURAL-PRODUCT SYNTHESIS; ORGANIC-SYNTHESIS; PROPARGYL ESTERS; METAL-CARBENE; FACILE ACCESS; IMINES; NITRONES; WATER; CYCLOPROPANES;

D O I：

10.1021/ol503169d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Cu(I)-catalyzed highly enantioselective [3 + 3] cycloaddition between two different 1,3-dipoles, phthalazinium dicyanomethanides and iminoester-derived azomethine ylides, has been achieved under mild reaction conditions, providing novel chiral heterocyclic compounds, 2,3,4,11b-tetrahydro-1H-pyrazino[2,1-a]phthalazine derivatives, in high yields with excellent diastereo- and enantioselectivies (up to 99% yield, 99% ee, >20:1 dr).

引用

页码：26 / 29

页数：4

共 56 条

[1] Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2014, 50 (83) :12434-12446

[2] Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides [J].

Adrio, Javier ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2011, 47 (24) :6784-6794

[3] Ionic liquids are compatible with on-water catalysis [J].

Beare, Kaitlin D. ;

Yuen, Alexander K. L. ;

Masters, Anthony F. ;

Maschmeyer, Thomas ;

McErlean, Christopher S. P. .

CHEMICAL COMMUNICATIONS, 2013, 49 (75) :8347-8349

[4] A NEW ACCESS TO PHOSPHAINDOLIZINES BY [3+2] CYCLOADDITION OF AZOMETHINE YLIDES ONTO PHOSPHAALKYNES [J].

BERGSTRASSER, U ;

HOFFMANN, A ;

REGITZ, M .

TETRAHEDRON LETTERS, 1992, 33 (08) :1049-1052

[5]

Buchanan GS, 2010, CURR ORG SYNTH, V7, P363

[6] Organic synthesis in water: 1,3-dipolar cycloaddition reactions at ambient temperature with aqueous suspensions of solid reactants [J].

Butler, Richard N. ;

Coyne, Anthony G. ;

Moloney, Eamon M. .

TETRAHEDRON LETTERS, 2007, 48 (20) :3501-3503

[7] Water and Organic Synthesis: A Focus on the In-Water and On-Water Border. Reversal of the In-Water Breslow Hydrophobic Enhancement of the Normal endo-Effect on Crossing to On-Water Conditions for Huisgen Cycloadditions with Increasingly Insoluble Organic Liquid and Solid 2π-Dipolarophiles [J].

Butler, Richard N. ;

Coyne, Anthony G. ;

Cunningham, William J. ;

Moloney, Eamon M. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3276-3291

[8] Water and the Huisgen cycloaddition reaction:: A focus on polar contributions to the transition state in the reactions of dicyano(phthalazinium)methanide with substituted styrenes and benzylidene acetones [J].

Butler, RN ;

Coyne, AG ;

Cunningham, WJ ;

Moloney, EM ;

Burke, LA .

HELVETICA CHIMICA ACTA, 2005, 88 (07) :1611-1629

[9] Kinetic and synthetic influences of water and solvent-free conditions on 1,3-dipolar cycloaddition reactions: the phthalazinium and pyridazinium dicyanomethanide 1,3-dipoles: surprisingly successful synthetic methods [J].

Butler, RN ;

Coyne, AG ;

Cunningham, WJ ;

Burke, LA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (11) :1807-1815

[10] The kinetic profile of phthalazinium-2-dicyanomethanide 1,3-dipole with 2π-dipolarophiles:: U-shaped dipolarophilic activity and classic type II dipole behaviour.: Reaction rates and DFT calculations [J].

Butler, RN ;

Coyne, AG ;

Burke, LA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (09) :1781-1784

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