Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid

Autor:	Sarah F. Jenkinson, George W. J. Fleet, Timothy J. R. Harris
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Regioselectivity Oxetane Catalysis Amino acid Inorganic Chemistry chemistry.chemical_compound chemistry Nucleophile SN2 reaction Organic chemistry Hydroxymethyl Azide Physical and Theoretical Chemistry Cis–trans isomerism
Zdroj:	Tetrahedron: Asymmetry. 15:2667-2679
ISSN:	0957-4166
Popis:	Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subsequent nucleophilic displacements of the corresponding triflates by azide proceeds in consistently excellent yields without any elimination to provide syntheses of scaffolds for a range of methyl and hydroxymethyl analogues of the antibiotic oxetin, a naturally occurring oxetane cis-β-amino acid. © 2004 Elsevier Ltd. All rights reserved.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6731905285393dcc2421f3f6301d634b https://doi.org/10.1016/j.tetasy.2004.07.031 Zobrazit plný text záznamu Full Text from ScienceDirect