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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
Full Text	PDF

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