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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 5
BKCSDE 23(5)
May 20, 2002 

 
Title
Introduction of a New Chiral Oxazolidin-2-one Derived from D-Mannitol and Its Applications as a Chiral Auxiliary
Author
Si-Min Kim, Hyunyong Jin, Jong-Gab Jun
Keywords
Oxazolidin-2-one, D-Mannitol, Alkylation, Aldol reaction, b-Lactam.
Abstract
Chiral oxazolidin-2-one is easily prepared from D-mannitol and demonstrated to undergo highly diastereoselective alkylation reactions via lithium imide Z-enolates of its N-acyl derivatives to afford α-branched products. Evans syn and non-Evans syn aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base. Also, this new auxiliary is employed in diastereoselective Staudinger-type β-lactam syntheses. Using 2-chloro-1-methylpyridinium iodide as the dehydrating agent, the reaction of auxiliary tethered acetic acid with trans imines gave the desired β-lactams with cis-selectivity.
Page
749 - 757
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