Ring opening of homochiral bicyclic oxazolidinones: Synthesis of allylglycinol derivatives

Abstract

(4R,6aS)-2-0xo-4-phenyl-2,4,5,6a,7-hexahydrooxazolo[3,2-c]oxazole and its it-methyl analog were synthesized using (R)-phenylglycinol and (S)-alaninol as the chiral source, respectively. The ring opening reaction of the bicyclic oxazolidinones by an allyltrimethylsilane-titanium tetrachloride mixture afforded the corresponding substitution products with diastereoselectivity of up to similar to 3:1. The major substitution product was readily converted to allylglycinol derivatives.