Scope of AuCl3 in the activation of per-O-acetylglycals

被引：58

作者：

Balamurugan, Rengarajan ^{[1
]}

Koppolu, Srinivasa Rao ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON | 2009年 / 65卷 / 39期

关键词：

GOLD-CATALYZED REACTIONS; STEREOSELECTIVE-SYNTHESIS; FERRIER REARRANGEMENT; ALLYLIC-REARRANGEMENT; FACILE SYNTHESIS; GLYCOSYLATION; GLYCALS; GLYCOSIDATION; ALKYNOPHILICITY; TRICHLORIDE;

D O I：

10.1016/j.tet.2009.07.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make beta-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：8139 / 8142

页数：4

相关论文

共 46 条

[11] A METHOD FOR THE SELECTIVE REDUCTION OF CARBOHYDRATE 4,6-O-BENZYLIDENE ACETALS [J].

DENINNO, MP ;

ETIENNE, JB ;

DUPLANTIER, KC .

TETRAHEDRON LETTERS, 1995, 36 (05) :669-672

[12]

Ferrier R.J., 2003, Org. React, V62, P569, DOI DOI 10.1002/0471264180.OR062.04

[13]

Ferrier RJ, 2001, TOP CURR CHEM, V215, P153

[14] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL [J].

FERRIER, RJ ;

PRASAD, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :570-&

[15] Ligand effects in homogeneous Au catalysis [J].

Gorin, David J. ;

Sherry, Benjamin D. ;

Toste, F. Dean .

CHEMICAL REVIEWS, 2008, 108 (08) :3351-3378

[16] Gold-catalyzed organic reactions [J].

Hashmi, A. Stephen K. .

CHEMICAL REVIEWS, 2007, 107 (07) :3180-3211

[17] The golden gate to catalysis [J].

Hoffmann-Röder, A ;

Krause, N .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) :387-391

[18] Propargyl glycosides as stable glycosyl donors: Anomeric activation and glycoside syntheses [J].

Hotha, Srinivas ;

Kashyap, Sudhir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9620-9621

[19] Gold-catalyzed cycloisomerizations of enynes:: A mechanistic perspective [J].

Jimenez-Nunez, Eloisa ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2008, 108 (08) :3326-3350

[20] Stereoselective synthesis of α-glucosides from 3-O-propargyl protected glucal exploiting the alkynophilicity of AuCl3 [J].

Kashyap, S ;

Hotha, S .

TETRAHEDRON LETTERS, 2006, 47 (12) :2021-2023

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