Highly functionalized cyclic and bicyclic β-amino acids from suga β-nitroesters

TETRAHEDRON

卷:76

Article

Otero, Jose M.¹  Estevez, Amalia M.¹  Estevez, Juan C.¹  Fleet, George W. J.²  Estevez, Ramon J.¹ 

[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Dept Quim Organ, Campus Vida, Santiago De Compostela 15782, Spain

[2] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

关键词: Nitro sugars;    Carbasugars;    beta-Amino acids;    3-Nitropropionic acids;    Molecular diversity;   

DOI  :  10.1016/j.tet.2019.130837

来源: Elsevier

【 摘 要 】

The synthesis of highly functionalized bicyclic and cyclic beta-amino acids from beta-nitrosugars is reported. Specifically, our strategy for the synthesis of polyhydroxylated cyclopentane beta-amino acids via the intramolecular C-alkylation of 6-nitro-2-O-triflates of furanosides has been applied to the preparation of the first two examples of a novel class of bicyclic beta-amino acids and a novel cyclopentene beta-amino acid. Also, our Henry reaction mediated strategy for the synthesis of polyhydroxylated cyclohexane beta-amino acids has been extended to a divergent, stereoselective synthesis of new polysubstituted cyclohexane and cyclopentane beta-amino acids. (C) 2019 Published by Elsevier Ltd.

【 授权许可】

Free