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

[11] Enantioselective hydrogenation of β-ketoesters with monodentate ligands [J].

Junge, K ;

Hagemann, B ;

Enthaler, S ;

Oehme, G ;

Michalik, M ;

Monsees, A ;

Riermeier, T ;

Dingerdissen, U ;

Beller, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) :5066-5069

[12] Synthesis of chiral monodentate binaphthophosphepine ligands and their application in asymmetric hydrogenations [J].

Junge, K ;

Hagemann, B ;

Enthaler, S ;

Spannenberg, A ;

Michalik, M ;

Oehme, G ;

Monsees, A ;

Riermeier, T ;

Beller, M .

TETRAHEDRON-ASYMMETRY, 2004, 15 (17) :2621-2631

[13] Synthesis of new chiral monodentate phosphines and their use in asymmetric hydrogenation [J].

Junge, K ;

Oehme, G ;

Monsees, A ;

Riermeier, T ;

Dingerdissen, U ;

Beller, M .

TETRAHEDRON LETTERS, 2002, 43 (28) :4977-4980

[14] Lewis acid catalyzed allylboration: Discovery, optimization, and application to the formation of stereogenic quaternary carbon centers [J].

Kennedy, JWJ ;

Hall, DG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (13) :4412-4428

[15]

OSBORN HMI, 1994, SYNLETT, P145

[16] Use of allenylphosphonates as new substrates for phosphane-catalyzed [3+2] and [4+2] annulations [J].

Panossian, Armen ;

Fleury-Bregeot, Nicolas ;

Marinetti, Angela .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (22) :3826-3833

[17] A promising new catalyst family for enantioselective cycloadditions involving allenes and imines:: chiral phosphines with transition metal-CH2-P:: linkages [J].

Scherer, Alexander ;

Gladysz, J. A. .

TETRAHEDRON LETTERS, 2006, 47 (36) :6335-6337

[18]

Segelstein B. E., 2005, U.S. Patent, Patent No. 2005272800

[19]

SHIM YK, 1990, SYNTHESIS-STUTTGART, P753

[20] Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates.: Part 1:: Formation of cis-aziridines [J].

Sweeney, JB ;

Cantrill, AA ;

McLaren, AB ;

Thobhani, S .

TETRAHEDRON, 2006, 62 (15) :3681-3693

← 1 2 3 →