Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline

Rubén Martín; Montserrat Alcón; Miquel A Pericàs; Antoni Riera

doi:10.1021/jo025832p

Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline

J Org Chem. 2002 Oct 4;67(20):6896-901. doi: 10.1021/jo025832p.

Authors

Rubén Martín¹, Montserrat Alcón, Miquel A Pericàs, Antoni Riera

Affiliation

¹ Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Parc Científic de Barcelona and Departament de Química Orgànica, Universitat de Barcelona, c/ Josep Samitier, 1-5, 08028-Barcelona, Spain.

PMID: 12353980
DOI: 10.1021/jo025832p

Abstract

The ring-closing metathesis (RCM) of two types of unsaturated chiral allylamines III, easily available from enantiomerically enriched epoxy alcohols, has been studied. Fully protected allylamines IIIa [(1)R = CH(2)-(CH(2))(n)()-CH=CH(2); (2)R = Boc; (3)R = PMB] have been prepared from unsaturated epoxy alcohols, whereas bis-allylamines IIIb ((1)R = Ph, (2)R = allyl,(3)R = Boc or PMB) have been prepared from 2,3-epoxy-3-phenylpropanol. Both types have been subjected to RCM to provide either cyclic allylamine I or II. The synthetic potential of these intermediates has been demonstrated by the enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline.