Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis-oxidation sequence

被引：38

作者：

Marco, JA

Carda, M

Rodríguez, S

Castillo, E

Kneeteman, MN

机构：

[1] Univ Valencia, Dept Q Organ, E-46100 Burjassot, Spain

[2] Univ Jaume 1, Dept Inorgan & Organ, E-12080 Castellon de La Plana, Spain

来源：

TETRAHEDRON | 2003年 / 59卷 / 23期

关键词：

ring-closing metathesis; allylic oxidation; conjugated gamma- and delta-lactones;

D O I：

10.1016/S0040-4020(03)00584-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic C-vinylation and C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted C=C bonds. These were then subjected to allylic oxidation to yield conjugated gamma- and delta-lactones. Reasons for the observed failures are presented and discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4085 / 4101

页数：17

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