Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates

作者：Miklos Ferenc; Mandity Istvan M; Sillanpaa Reijo; Fueloep Ferenc

来源：Tetrahedron Letters, 2013, 54(29): 3769-3772.

DOI：10.1016/j.tetlet.2013.05.009

• Oxidative cleavage
• beta-Aminotricarboxylic acid
• Isomerization
• Epimerization
• Potassium permanganate oxidation

The sterically controlled oxidative cleavage of N-protected diexo- and diendo-substituted norbornene beta-amino acids/esters resulted in four trimethyl 3-aminocyclopentane-1,2,4-carboxylate diastereomers. The sodium methoxide mediated isomerization of the four diastereomers in all cases yielded the thermodynamically most stable all-trans stereoisomer as a single product.

• 出版日期2013-7-17