Room temperature intramolecular hydro-O-alkylation of aldehydes:: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization

被引：133

作者：

Pastine, SJ ^{[1
]}

Sames, D ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 24期

关键词：

D O I：

10.1021/ol0522283

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope and limitations of intramolecular hydro-O-alkylation of aldehyde substrates leading to spiroketals and bicyclic ketals and aminals is reported. The direct transformation of tertiary and sterically hindered secondary sp(3) C-H bonds into C-O bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

引用

页码：5429 / 5431

页数：3

共 12 条

[1] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].