Catalytic asymmetric addition of β-keto phosphonates to an activated imine—formation of optically active functionalized phosphonate α-amino acid derivatives,10.1039/B416294C

热搜：

Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Catalytic asymmetric addition of β-keto phosphonates to an activated imine—formation of optically active functionalized phosphonate α-amino acid derivatives

Anne Kjærsgaard,Karl Anker Jørgensen

Organic & Biomolecular Chemistry Pub Date : 01/24/2005 00:00:00 , DOI:10.1039/B416294C

Abstract

The direct stereoselective addition of an activated imine to β-keto phosphonates in the presence of chiral Lewis acid complexes is developed. The evaluation of different activated imines shows that an N-tosyl-α-imino ester adds in a diastereo- and enantioselective fashion to β-keto phosphonates activated by especially chiral copper(II)-bisoxazoline complexes. An evaluation of Lewis acids, chiral ligands and reaction conditions, such as solvent, bases and other additives, shows that high yields, moderate diastereoselectivity and good enantioselectivity are obtained. The scope of the reaction is demonstrated for the reaction of β-keto phosphonates and finally, the mechanism for the catalytic stereoselective step is presented.