METAL-ASSISTED ALDOL CONDENSATION OF CHIRAL 6-METHYL PERIHYDROPYRIMIDIN-4-ONES

被引：8

作者：

AMOROSO, R ^{[1
]}

CARDILLO, G ^{[1
]}

MOBBILI, G ^{[1
]}

TOMASINI, C ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOL,VIA SELMI 2,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(00)80074-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of 6-methyl perihydropyrimidin-4-ones (1'S,6R)-3a and (1'S,6S)-3b is reported starting from rac-3-aminobutanoic acid. The aldol condensation of various metal enolates of 3a and 3b with benzaldehyde and acetaldehyde is reported. All reactions afford complete facial diastereoselectivity and good simple diastereoselectivity, depending on the nature of the enolate and of the aldehyde. The reaction yields are generally good and the aldols have been characterized by means of H-1 NMR spectroscopy and NOEDIFF experiments.

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页码：2241 / 2254

页数：14

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