An Aliphatic Bischler-Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

被引：2

作者：

Amer, Mostafa M. ^{[1
]}

Olaizola, Olatz ^{[1
]}

Carter, Jennifer ^{[1
]}

Abas, Hossay ^{[1
]}

Clayden, Jonathan ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 01期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

D O I：

10.1021/acs.orglett.9b04250

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-chloroformylimidazolidinone derivative of enantiopure L-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel-Crafts-type acylation that corresponds to an aliphatic Bischler-Napieralski reaction. The product 3,4-dihydropyridinones were amenable to further functionalization, and finally hydrolysis, to deliver a series of enantio-enriched pipecolic acid derivatives.

引用

页码：253 / 256

页数：4

共 21 条

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