The Synthesis of AraBOX, a New 4,4′-Bis(oxazoline), from Novel Pentitol-Derived Bis-β-amino Alcohols

Autor:	Fiona Kirby, Patrick McArdle, David Frain, Patrick O'Leary
Rok vydání:	2009
Předmět:	chemistry.chemical_compound chemistry Stereochemistry Ligand Organic Chemistry Enantioselective synthesis Alcohol Oxazoline Ring (chemistry) Xylitol Benzamide Catalysis
Zdroj:	Synlett. 2009:1261-1264
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0029-1216731
Popis:	The preparation of a novel phenyl 4,4'-bis(oxazoline) [AraBOX] is described. The novel ligand is prepared in two efficient steps from a bis-[(O-silyl)β-amino alcohol], via conversion into an intermediate bis(benzamide) followed by a one-pot deprotection-activation-ring closure (DARC) oxazoline formation. To our knowledge, this is the first reported synthesis of an oxazoline ring via this DARC method. The synthesis of two precursor bis-β-amino alcohols, (2R,4R)- and meso-2,4-diaminopentane-1,5-diol, derived from D-(+)-arabitol and xylitol, respectively, is also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4a61180f6d4f40f627ee968b2dfcb22b https://doi.org/10.1055/s-0029-1216731 Zobrazit plný text záznamu