Stereoselective synthesis of 4-piperidone and 4-aminotetrahydropyridine derivatives by the imino Diels-Alder reaction of 2-amino-1,3-butadienes

来自 ACS

阅读量:

7

作者:

J BarluengaF AznarC. ValdésM. Cabal

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摘要:

2-Amino-4-(alkoxymethyl)-1,3-butadienes react smoothly with nonactivated aldimines derived from aromatic aldehydes in the presence of ZnCl 2 as Lewis acid giving rise, with good yields and very high stereoselectivity, to substituted 4-aminotetrahydropyridines which upon hydrolysis yield 4-piperidone derivatives. Moreover, the stereochemistry of the cyclization process depends on the nature of the N-substituent of the imine

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DOI:

10.1021/JO00064A030

年份:

1993

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