Diastereoselective Synthesis of Highly Substituted 2,5-Diaminohexanes via Nitrile Oxide Cycloaddition to a Vinylogous Amino Acid

Erwin P. Schreiner; Hubert Gstach

doi:10.1055/s-1996-5670

Synlett 1996; 1996(11): 1131-1133
DOI: 10.1055/s-1996-5670

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Diastereoselective Synthesis of Highly Substituted 2,5-Diaminohexanes via Nitrile Oxide Cycloaddition to a Vinylogous Amino Acid

Erwin P. Schreiner^* , Hubert Gstach

^*SANDOZ Forschungsinstitut, Brunnerstraße 59, A-1235 Vienna, Austria, Fax +43(1)86 634 354, e-mail schreiner_e@a1.wienv1.sandoz.com

Abstract

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A novel route to 1,6-disubstituted 2,5-diamino-3-hydroxy-4-hydroxymethylhexanes is described. N-protected ethyl (2E,4S)-4-amino-5-phenylpent-2-enoate undergoes cycloaddition with nitrile oxides producing the syn and anti isomers of ethyl isoxazoline-4-carboxylates in a 2:1 ratio. The individual isomers are converted into 1,4-diaminohexanes via chemoselective ester reduction with lithium aluminum hydride, followed by highly diastereoselective reductive cleavage of the isoxazoline ring with borane-dimethylsulfide complex.

vinylogous amino acid - nitrile oxide - isoxazoline - reduction - borane-dimethylsulfide complex

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