Chiral 1,2,4-triazole derivatives as potential synthetic intermediates

Alan R. Katritzky; Jin Wang; Peter Leeming; Peter J. Steel

doi:10.1016/0957-4166(96)00197-8

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Chiral 1,2,4-triazole derivatives as potential synthetic intermediates

Journal article

Peer reviewed

Chiral 1,2,4-triazole derivatives as potential synthetic intermediates

Alan R. Katritzky, Jin Wang, Peter Leeming and Peter J. Steel

Tetrahedron: asymmetry, Vol.7(6), pp.1631-1640

01/06/1996

DOI: https://doi.org/10.1016/0957-4166(96)00197-8

Abstract

chiral triazole

diastereoselectivity

heterocycle

α-substituted α-amino acids

The potential of (S,S)-3,5-bis(α-trimethylsilyloxyethyl)-1,2,4-triazole 3 and (S,S)-3,5-bis(α-methoxyethyl)-1,2,4-triazole 9 as chiral synthetic intermediates has been investigated. Reaction of the chiral triazole 3 with ethyl 2-bromopropionate and subsequent treatment with LDA followed by quenching with an electrophile gave either esters 5 or lactones 6&7 in good yields with generally excellent diastereoselectivities. Graphic

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Title: Chiral 1,2,4-triazole derivatives as potential synthetic intermediates
Creators - without role: Alan R. Katritzky - University of Florida
Jin Wang - University of Florida
Peter Leeming - University of Florida
Peter J. Steel - University of Canterbury
Publication Details: Tetrahedron: asymmetry, Vol.7(6), pp.1631-1640
Publisher: Elsevier Ltd
Identifiers: 9934562308331
Academic Unit: King Abdulaziz University
Language: English
Resource Type: Journal article