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Communication | Regular issue | Vol 27, No. 9, 1988, pp.2099-2102
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4654
Asymmetric Induction by Chiral Heterocyclic Compounds: Reaction of Chiral N-Methyl-4-phenyl-1,3-oxazolidines with Organometallic Reagents

Hiroshi Takahashi,* Hiroyuki Niwa, and Kimio Higashiyama

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


The reaction of (2S,4R)-2-alkyl-N-methyl-4-phenyl-1,3-oxazolidines (1a-c) with Grignard reagent gave (1R,1’R)-form compounds (2a-c) as the major product. On the contrary, the reaction of 1a-c with organotitanium reagent gave (1S,1’R)-form compounds (3a-c) as the major product. This stereoselectivity is a remarkable characteristic of the reaction of 1,3-oxazolidines with organometallic reagents.