Diels-Alder Reactions of α-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene

被引：11

作者：

Abas, Hossay ^{[1
]}

Frampton, Christopher S. ^{[2
]}

Spivey, Alan C. ^{[1
]}

机构：

[1] Imperial Coll London, Dept Chem, South Kensington SW7 2AZ, England

[2] Brunel Univ, Wolfson Ctr Mat Proc, Kingston Lane, Uxbridge UB8 3PH, Middx, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

LEWIS-ACID; DERIVATIVES; ANALOGS;

D O I：

10.1021/acs.joc.6b01684

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermal Diels-Alder reactions of a-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene have been explored to investigate the factors influencing the endo/exo selectivity. For the dihydropyridine, steric factors allowed the diastereoselectivity to be modulated to favor either endo- or exo-ester adducts. For cyclopentadiene, the endo-ester adducts were favored regardless of steric perturbation, although catalysis by bulky Lewis acids increased the proportion of exo-ester adducts in some cases. These Lewis acids were incompatible with the dihydropyridine diene as they induced its decomposition.

引用

页码：9947 / 9956

页数：10

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