Intramolecular 1,5-versus 1,6-hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrate models

被引：52

作者：

Francisco, CG ^{[1
]}

Freire, R ^{[1
]}

Herrera, AJ ^{[1
]}

Peréz-Martín, I ^{[1
]}

Suárez, E ^{[1
]}

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 38206, Tenerife, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 11期

关键词：

D O I：

10.1021/ol025981u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The alkoxy radical generated by reaction of 3,7-anhydro-2-deoxyoctitols with (diacetoxyiodo)benzene (DIB) and iodine abstracts regioselectively either the proton at C7 or that at C4 depending on the electronegativity of the substituent at C4. The correct election of this substituent can switch the reaction to give 2,9-dioxabicyclo[3.3.1]nonane or hexahydro-2H-furo[3,2-b]pyran ring systems.

引用

页码：1959 / 1961

页数：3

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