Stereo- and regiochemistry in the (asymmetric) cycloaddition reaction of 5-chloro-2(1H)-pyrazinones with cyclic and monosubstituted alkenes and with a N-acryloyl substituted chiral auxiliary

被引：8

作者：

Rombouts, FJR ^{[1
]}

Vanraes, DAJ ^{[1
]}

Wynendaele, J ^{[1
]}

Loosen, PK ^{[1
]}

Luyten, I ^{[1
]}

Toppet, S ^{[1
]}

Compernolle, F ^{[1
]}

Hoornaert, GJ ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Dept Organ Chem, B-3001 Louvain, Belgium

来源：

TETRAHEDRON | 2001年 / 57卷 / 15期

关键词：

pyrazinones; Diels-Alder reactions; bicyclic heterocyclic compounds; chiral auxiliary;

D O I：

10.1016/S0040-4020(01)00179-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloaddition of 5-chloro-2(1H)-pyrazinones 1 with various dienophiles was used to generate the corresponding 2,5-diazabicyclo[2.2.2]octanes. Following reduction or hydrolysis of the bridged adducts, the regio- and stereochemical structure was determined by analysis of the coupling and NOE patterns in the H-1 NMR spectra. With symmetric dienophiles the endo adducts are formed exclusively. The regiochemistry for the reaction of 1 with methyl acrylate and ethyl vinyl ether, and the asymmetric induction found with the N-acryloyl substituted chiral auxiliary (4S)-4-isopropyl-1-methyltetrahydro-2H-imidazol-2-one, largely depend on the electron donating or attracting properties and size of the 3-substituents of i. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3209 / 3220

页数：12

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