Enantioselective synthesis of highly functionalized 4-piperidones by the asymmetric imino-diels-alder reaction of chiral 2-amino-1,3-butadienes

被引：35

作者：

Barluenga, J ^{[1
]}

Aznar, F ^{[1
]}

Ribas, C ^{[1
]}

Valdes, C ^{[1
]}

Fernandez, M ^{[1
]}

Cabal, MP ^{[1
]}

Trujillo, J ^{[1
]}

机构：

[1] UNIV LA LAGUNA,INST UNIV BIOORGAN,CTR PROD NAT ORGAN ANTONIO GONZALEZ,LA LAGUNA 38206,TENERIFE,SPAIN

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 1996年 / 2卷 / 07期

关键词：

asymmetric Diels-Alder reactions; butadienes; Diels-Alder reactions; piperidones;

D O I：

10.1002/chem.19960020712

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral 2-amino-1,3-butadienes 1 derived from commercially available (S)-2-methoxymethylpyrrolidine react with aromatic N-trimethylsilylaldimines and phenylaldimines in the presence of ZnCl2 to give, after the reaction workup. 4-piperidones 4 and 6, respectively, with moderate to very high enantiomeric excesses. In addition, the absolute configurations of derivatives of 4a and 4g were determined by circular dichroism and NMR spectroscopy on the Mosher ester, respectively.

引用

页码：805 / 811

页数：7

共 39 条

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