Synthesis of perhydro-furo[2,3-b]pyran (and furan)-3-yl methanols by oxygenative radical cyclization

被引：30

作者：

Mayer, S

Prandi, J

Bamhaoud, T

Bakkas, S

Guillou, O

机构：

[1] Univ Orleans, Inst Chim Organ & Analyt, F-45067 Orleans 2, France

[2] Univ Chouaib Doukkali, Lab Chim Organ & Bioorgan, El Jadida, Morocco

[3] INSA, Lab Chim Materiaux Inorgan & Cristallog, F-35043 Rennes, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 30期

关键词：

D O I：

10.1016/S0040-4020(98)00478-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-exo radical cyclization followed by oxygenation with molecular oxygen of various 3-halogeno-2-allyloxy-perhydro-pyrans and -furans gave the perhydro-furo[2,3-b]pyran (and furan)-3-yl methanols in one step. Two catalytic systems were efficiently used for this transformation : tributyltin hydride/AIBN/O-2 and Co(salen)/NaBH4/O-2. Yields were high and interesting selectivities were observed. The reaction is general and was successfully applied to carbohydrate derived substrates. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

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收藏

页码：8753 / 8770

页数：18

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