Enantioselective Preparation of cis-β-Azidocyclopropane Esters by Cyclopropanation of Azido Alkenes Using a Chiral Dirhodium Catalyst

被引：49

作者：

Gu, Peiming ^{[1
,2
,3
]}

Su, Yan ^{[1
,2
,3
]}

Wu, Xiu-Ping ^{[1
,2
]}

Sun, Jian ^{[1
,2
]}

Liu, Wanyi ^{[1
,2
]}

Xue, Ping ^{[1
,2
]}

Li, Rui ^{[1
,2
]}

机构：

[1] Ningxia Univ, Key Lab Energy Sources & Engn, State Key Lab Cultivat Base Nat Gas Convers, Yinchuan 750021, Peoples R China

[2] Ningxia Univ, Dept Chem, Yinchuan 750021, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 09期

关键词：

AMINOCYCLOPROPANE CARBOXYLIC-ACIDS; ASYMMETRIC CYCLOPROPANATION; RUTHENIUM; PEPTIDES; LIGANDS; RING;

D O I：

10.1021/ol3006437

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereo- and enantiocontrolled preparation of the conformationally restricted cis-beta-azidocyclopropane esters have been developed. The Rh-2(S-DOSP)(4) was found to be an efficient catalyst in hexane for the cyclopropanation of azido alkenes with diazo esters, and 19 cis-beta-azidocyclopropane esters were prepared in excellent yields. The value of the diastereomer ratio was up to 99:1, and the enantiomeric excess was up to 95%. Furthermore, the relative and absolute configuration was confirmed by X-ray analysis.

引用

页码：2246 / 2249

页数：4

共 22 条

[11] Chiral monodentate phosphoramidite ligands control the absolute configuration at pseudotetrahedral ruthenium: asymmetric catalytic cyclopropanation of olefins [J].

Huber, D ;

Mezzetti, A .

TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2193-2197

[12] Analogues of neuropeptide Y containing β-aminocyclopropane carboxylic acids are the shortest linear peptides that are selective for the Y1 receptor [J].

Koglin, N ;

Zorn, C ;

Beumer, R ;

Cabrele, C ;

Bubert, C ;

Sewald, N ;

Reiser, O ;

Beck-Sickinger, AG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (02) :202-+

[13] Stereoselective cyclopropanation reactions [J].

Lebel, H ;

Marcoux, JF ;

Molinaro, C ;

Charette, AB .

CHEMICAL REVIEWS, 2003, 103 (04) :977-1050

[14] Michael-induced ring closure to 2-azidocyclopropane-1,1-dicarboxylates and their staudinger reduction to 5-alkoxy-3-(alkoxycarbonyl)pyrrolidin-2-ones [J].

Mangelinckx, S ;

De Kimpe, N .

SYNLETT, 2006, (03) :369-374

[15] Diastereoselective synthesis of 1-aryl-2-amino-cyclopropane carboxylates [J].

Melby, Trude ;

Hughes, Rachael Anne ;

Hansen, Tore .

SYNLETT, 2007, (14) :2277-2279

[16] trans-cyclopropyl β-amino acid derivatives via asymmetric cyclopropanation using a (salen)Ru(II) catalyst [J].

Miller, JA ;

Hennessy, EJ ;

Marshall, WJ ;

Scialdone, MA ;

Nguyen, ST .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7884-7886

[17]

PAULINI K, 1991, LIEBIGS ANN CHEM, P455

[18] Recent developments in asymmetric cyclopropanation [J].

Pellissier, Helene .

TETRAHEDRON, 2008, 64 (30-31) :7041-7095

[19]

Shltama H., 2007, CHEM-EUR J, V13, P4849

[20] Facile synthesis of β-azidocyclopropanecarboxylates by MIRC reaction [J].

Su, JT ;

Qiu, GF ;

Liang, SC ;

Hu, XM .

SYNTHETIC COMMUNICATIONS, 2005, 35 (11) :1427-1433

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