Acid-catalyzed Grob fragmentation reactions of acetonides derived from terpenes

被引：14

作者：

Barluenga, J ^{[1
]}

Alvarez-Pérez, M ^{[1
]}

Wuerth, K ^{[1
]}

Rodríguez, F ^{[1
]}

Fañanás, FJ ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33006 Oviedo, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol034083a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetonides derived from different terpenes undergo Grob fragmentation by treatment with a catalytic amount of acid, triflic acid, or boron trifluoride, giving aldehydes containing a cyclopropane or cyclobutane ring with good yields and complete diastereoselectivity. The structure and the stereochemistry of the starting acetonide have a crucial influence on the reaction course.

引用

页码：905 / 908

页数：4

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