Regioselective ring opening of amino epoxides with nitriles: an easy synthesis of (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols with differently protected amine functions

José M Concellón; José Ramón Suárez; Virginia Del Solar

doi:10.1021/jo051109y

Regioselective ring opening of amino epoxides with nitriles: an easy synthesis of (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols with differently protected amine functions

J Org Chem. 2005 Sep 2;70(18):7447-50. doi: 10.1021/jo051109y.

Authors

José M Concellón¹, José Ramón Suárez, Virginia Del Solar

Affiliation

¹ Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain. jmcg@fq.uniovi.es

PMID: 16122275
DOI: 10.1021/jo051109y

Abstract

[reaction: see text] Transformation of enantiopure (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides 1 or 2 into the corresponding (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols 3 or 4 is described. The opening of the epoxide ring with different nitriles (Ritter reaction) takes place with total selectivity and in high yields in the presence of BF3.Et2O. Interestingly, the two amine groups are differently protected. A mechanism to explain this transformation is proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines
Epoxy Compounds
HIV Protease Inhibitors / chemical synthesis*
Molecular Conformation
Nitriles
Stereoisomerism

Substances

Amines
Epoxy Compounds
HIV Protease Inhibitors
Nitriles