Highly stereoselective cyclopropanation of glycals with cyclic diazoamides: a facile synthesis of spirooxindolyl sugar derivatives

被引：39

作者：

Reddy, B. V. Subba ^{[1
]}

Rajasekaran, Tamilselvan ^{[1
]}

Karthik, Govindaraju ^{[1
]}

Rao, T. Prabhakar ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Ctr Nucl Magnet Resonance Spect, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 27期

关键词：

Cyclopropanation; Glycals; Rhodium(II) acetate; Spirooxindoles; Diazoamides; DIASTEREOSELECTIVE SYNTHESIS; UNSATURATED SUGARS; ORGANIC-SYNTHESIS; RING-EXPANSION; POTENT;

D O I：

10.1016/j.tetlet.2012.04.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II) acetate catalyzed intermolecular cyclopropanation of glycals with cyclic carbenoids generated from 3-diazo-2-oxindole has been achieved to produce a novel series of spirooxindolyl sugar derivatives in good yields under mild experimental conditions. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3416 / 3420

页数：5

共 23 条

[1]

Badillo JJ, 2010, CURR OPIN DRUG DISC, V13, P758

[2]

Baidzhigitova E.A., 1981, IZV AKAD NAUK KIRG S, P50

[3] Synthesis and chemistry of cyclopropanated carbohydrates [J].

Cousins, GS ;

Hoberg, JO .

CHEMICAL SOCIETY REVIEWS, 2000, 29 (03) :165-174

[4] New aspects of catalytic asymmetric cyclopropanation [J].

Doyle, MP ;

Protopopova, MN .

TETRAHEDRON, 1998, 54 (28) :7919-7946

[5] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[6] Cyclopropanation of unsaturated sugars with ethyl diazoacetate [J].

Hoberg, JO ;

Claffey, DJ .

TETRAHEDRON LETTERS, 1996, 37 (15) :2533-2536

[7] CYCLOPROPANATION AND RING-EXPANSION OF UNSATURATED SUGARS [J].

HOBERG, JO ;

BOZELL, JJ .

TETRAHEDRON LETTERS, 1995, 36 (38) :6831-6834

[8] Formation of seven-membered oxacycles through ring expansion of cyclopropanated carbohydrates [J].

Hoberg, JO .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6615-6618

[9] Stereoselective cyclopropanation reactions [J].

Lebel, H ;

Marcoux, JF ;

Molinaro, C ;

Charette, AB .

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

[10] Total synthesis of (-)-spirotryprostatin B: Synthesis and related studies [J].

Marti, C ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11505-11515

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