Enantioselective Binaphthophosphepine-Promoted [3+2] Annulations of N-Ts- and N-DPP-Imines with Allenoates and 2-Butynoates

被引：81

作者：

Pinto, Nathalie ^{[1
]}

Fleury-Bregeot, Nicolas ^{[1
]}

Marinetti, Angela ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 01期

关键词：

Phosphanes; Asymmetric catalysis; 3+2] Cyclisations; Allenes; Imines; NITROGEN-HETEROCYCLES; CHIRAL PHOSPHINES; ACID-DERIVATIVES; ALLENES; LIGANDS; CYCLOADDITION; HYDROGENATION; CATALYSIS; 2,3-BUTADIENOATES; AZIRIDINES;

D O I：

10.1002/ejoc.200800598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of binaphthophosphepine la as a catalyst for the [3+2] cyclisation between allenoates or 2-butynoates and imines was investigated. The effects of the imine protecting group on both the catalytic activity and enantioselectivity were-determined by comparing the behaviour of N-tosyl- and N-DPP-imines. The N-DPP-imines displayed lower reactivity, but afforded the desired pyrrolines in higher enantiomeric excess (73-92% ee). The DPP protecting group was removed from the final pyrrolines under mild conditions to afford the corresponding secondary amines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：146 / 151

页数：6

共 28 条

[1] Expanding the scope of atropisomeric monodentate P-donor ligands in asymmetric catalysis:: Hydrogen-transfer reduction of α,β-unsaturated acid derivatives by rhodiuni/Ph-binepine catalysts [J].

Alberico, Elisabetta ;

Nieddu, Ilenia ;

Taras, Rossana ;

Gladiali, Serafino .

HELVETICA CHIMICA ACTA, 2006, 89 (08) :1716-1729

[2] Stereoselective synthesis of α-silylamines by the direct addition of silyl anions to activated Imines [J].

Ballweg, DM ;

Miller, RC ;

Gray, DL ;

Scheidt, KA .

ORGANIC LETTERS, 2005, 7 (07) :1403-1406

[3] Small-molecule inhibitors of protein geranylgeranyltransferase type I [J].

Castellano, Sabrina ;

Fiji, Hannah D. G. ;

Kinderman, Sape S. ;

Watanabe, Masaru ;

de Leon, Pablo ;

Tamanoi, Fuyuhiko ;

Kwon, Ohyun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5843-+

[4] Development of practical rhodium phosphine catalysts for the hydrogenation of β-dehydroamino acid derivatives [J].

Enthaler, Stephan ;

Erre, Giulia ;

Junge, Kathrin ;

Holz, Jens ;

Boerner, Armin ;

Alberico, Elisabetta ;

Nieddu, Ilenia ;

Gladiali, Serafino ;

Beller, Matthias .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :568-577

[5] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions [J].

Fang, Yuan-Qing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5660-+

[6] Screening of chiral phosphines as catalysts for the enantioselective [3+2] annulations of N-tosylimines with allenic esters [J].

Fleury-Bregeot, Nicolas ;

Jean, Ludovic ;

Retailleau, Pascal ;

Marinetti, Angela .

TETRAHEDRON, 2007, 63 (48) :11920-11927

[7] NOVEL ATROPISOMERIC PHOSPHORUS LIGANDS - 4,5-DIHYDRO-3H-DINAPHTHO[2,1-C,1',2'-E]PHOSPHEPINE DERIVATIVES [J].

GLADIALI, S ;

DORE, A ;

FABBRI, D ;

DELUCCHI, O ;

MANASSERO, M .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :511-514

[8]

HUMPHREY JM, 2005, Patent No. 2005115976

[9] Phosphine-catalyzed enantioselective [3+2] annulations of 2,3-butadienoates with imines [J].

Jean, L ;

Marinetti, A .

TETRAHEDRON LETTERS, 2006, 47 (13) :2141-2145

[10] THE TITANIUM TETRACHLORIDE INDUCED SYNTHESIS OF N-PHOSPHINOYLIMINES AND N-SULPHONYLIMINES DIRECTLY FROM AROMATIC-ALDEHYDES [J].

JENNINGS, WB ;

LOVELY, CJ .

TETRAHEDRON, 1991, 47 (29) :5561-5568

← 1 2 3 →