Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones

被引：139

作者：

Llamas, T ^{[1
]}

Arrayás, RG ^{[1
]}

Carretero, JC ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 09期

关键词：

D O I：

10.1021/ol060314c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sultones is described. Nearly complete exo selectivity and enantioselectivities up to 85% ee are attained with Cu(CH3CN)(4)ClO4/Taniaphos as the catalyst system. The resulting enantioenriched 3-sulfonyl cycloadducts are versatile intermediates in the synthesis of 2,5-disubstituted pyrrolidines.

引用

页码：1795 / 1798

页数：4

共 38 条

[1] Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes [J].

Cabrera, S ;

Arrayás, RG ;

Carretero, JC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3944-3947

[2] Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].

Cabrera, S ;

Arrayás, RG ;

Alonso, I ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947

[3] Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides [J].

Cabrera, S ;

Arrayás, RG ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16394-16395

[4] Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].

Chen, C ;

Li, XD ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175

[5] Heterocyclic enamines: The versatile intermediates in the synthesis of heterocyclic compounds and natural products [J].

Cheng, Y ;

Huang, ZT ;

Wang, MX .

CURRENT ORGANIC CHEMISTRY, 2004, 8 (04) :325-351

[6] Nonstabilized N-unsubstituted azomethine ylides:: A synthesis of indolizidine 239CD [J].

Clark, RB ;

Pearson, WH .

ORGANIC LETTERS, 1999, 1 (02) :349-351

[7] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].

Feringa, BL .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353

[8] MULTIPLY CONVERGENT SYNTHESES VIA CONJUGATE-ADDITION REACTIONS TO CYCLOALKENYL SULFONES [J].

FUCHS, PL ;

BRAISH, TF .

CHEMICAL REVIEWS, 1986, 86 (05) :903-917

[9] Cu(I)-catalyzed highly exo-selective and enantioselective [3+2] cycloaddition of azomethine ylides with acrylates [J].

Gao, WZ ;

Zhang, XM ;

Raghunath, M .

ORGANIC LETTERS, 2005, 7 (19) :4241-4244

[10]

Gothelf AS, 2002, ANGEW CHEM INT EDIT, V41, P4236, DOI 10.1002/1521-3773(20021115)41:22<4236::AID-ANIE4236>3.0.CO

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