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http://dx.doi.org/10.5012/bkcs.2002.23.5.749

Introduction of a New Chiral Oxazolidin-2-one Derived from D-Mannitol and Its Applications as a Chiral Auxiliary  

Kim, Si-Min
Jin, Hyun-Yong
Jun, Jong-Gab
Publication Information
Bulletin of the Korean Chemical Society / v.23, no.5, 2002 , pp. 749-757 More about this Journal
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 ${\alpha}-branched$ products. Evans syn and non-Evans sy n 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 ${\beta}-lactam$ syntheses. Using 2-chloro-1-methylpyridinium iodide as the dehydrating agent, the reaction of auxiliary tethered acetic acid with trans imines gave the desired ${\beta}-lactams$ with cis-selectivity.
Keywords
Oxazolidin-2-one; D-Mannitol; Alkylation; Aldol reaction; $\beta$-Lactam;
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