1, 2-vs. 1, 4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)-and 2-cinnamyl-1, 3-oxazolidines

LN Pridgen, MK Mokhallalati…

Index: Pridgen, Lendon N.; Mokhallalati, Mohamed K.; Wu, Ming-Jung Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1237 - 1241

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Citation Number: 76

Abstract

" Diastereomeric ratios were determined by 400-MHz'H NMR. The enantiomeric excess was determined using (R)-BNPPA as the shift reagent as reported by S hapir~.~ study, we demonstrated how one could subsequently obtain, via oxidative cleavage of 2 (Scheme I), a- arylalkylamines 3 in high enantiomeric excess. We now report that during the course of that study, we observed that 2-(l-naphthyl) derivatives of 1 underwent exclusively 1,. l-addition ...