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Mandatory Fields
Frain, D,Kirby, F,McArdle, P,O'Leary, P
2009
May
Synlett
The Synthesis of AraBOX, a New 4,4 '-Bis(oxazoline), from Novel Pentitol-Derived Bis-beta-amino Alcohols
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Optional Fields
asymmetric synthesis ligand catalysis oxazoline chiral pool CHIRAL GLYCINE EQUIVALENTS PURE 4-AMINOGLUTAMIC ACIDS ASYMMETRIC CATALYSIS OPERATIONALLY CONVENIENT BIS(OXAZOLINE) LIGANDS CONJUGATE ADDITIONS CYCLOPROPANATION EFFICIENT DICHLOROMETHANE DERIVATIVES
1261
1264
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)beta-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-beta-amino alcohols, (2R,4R)- and meso-2,4-diaminopentane-1,5-diol, derived from D-(+)-arabitol and xylitol, respectively, is also described.
DOI 10.1055/s-0029-1216731
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