Tandem alkylation-cyclization process via an O,C-dianion

被引：4

作者：

Banaag, AR

Berger, GO

Dhoro, F

delos Santos, DB

Dixon, DD

Mitchell, JP

Tokeshi, BK

Tius, MA

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA

来源：

TETRAHEDRON | 2005年 / 61卷 / 13期

基金：

美国国家卫生研究院;

关键词：

allene; nazarov; cyclization;

D O I：

10.1016/j.tet.2005.01.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the gamma carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3419 / 3428

页数：10

共 9 条

[1] PHOTOCHEMICAL TRANSFORMATIONS .24. SYNTHESIS OF 18-HYDROXYOESTRONE [J].