Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

被引：14

作者：

Ramakrishna, Bandi ^{[1
]}

Sridhar, Perali Ramu ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 17期

关键词：

STEREOSELECTIVE-SYNTHESIS; ENANTIOMERICALLY PURE; C-GLYCOSIDES; TETRAHYDROFURANS; PYRANOSIDES; CHEMISTRY; STRATEGY; ACCESS; ETHERS; KETONE;

D O I：

10.1021/ol402021e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

引用

页码：4474 / 4477

页数：4