Highly Diastereoselective Alkylation of Perhydropyrimidin-4-ones Directed toward the Synthesis of. alpha.-Substituted. beta.-Amino Acids. 2.

I Braschi, G Cardillo, C Tomasini…

Index: Braschi; Cardillo; Tomasini; Venezia Journal of Organic Chemistry, 1994 , vol. 59, # 24 p. 7292 - 7298

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Citation Number: 14

Abstract

The alkylation of several enantiomerically pure perhydropyrimidin-4-ones at C5 is described. For the methylation reaction, mixtures of 5, 6-trans-and cis-disubstituted adducts were obtained with high diastereomeric ratios, whereas only the 5, 6-trans-disubstituted products were obtained with larger alkylating agents. The dialkylation reaction at C5 was also studied, and the 5, 6-cistrisubstituted product was preferentially formed. Acidic ...