β-iodoallenolates as Springboards for Annulation Reactions

被引：30

作者：

Ciesielski, Jennifer ^{[1
]}

Canterbury, Daniel P. ^{[1
]}

Frontier, Alison J. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 19期

关键词：

BAYLIS-HILLMAN REACTION; FUNGUS PHOMA SP; ALDOL REACTION; ALPHA; BETA-ACETYLENIC KETONES; STEREOSELECTIVE-SYNTHESIS; ACETYLENIC KETONES; CARBONYL-COMPOUNDS; ALDEHYDES; CYCLIZATION; CATALYST;

D O I：

10.1021/ol901721y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-lodoallenolates II, generated from alkynones I with tetra-n-butylammonium iodide and a Lewis acid, underwent selective single or double annulation, depending on the Lewis acid promoter. Treatment with TiCl4 gave cyclohexenyl alcohols III, whereas BF3 center dot OEt2 gave oxadecalins IV. The scope and limitations of the two annulation reactions are described.

引用

页码：4374 / 4377

页数：4

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