A novel reaction of α-haloepoxides with trialkylstannates

LD Corey, SM Singh…

Index: Corey, L. D.; Singh, S. M.; Oehlschlager, A. C. Canadian Journal of Chemistry, 1987 ,  vol. 65, p. 1821 - 1827

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Citation Number: 14

Abstract

The reaction of α-haloepoxides with zinc powder or reagents containing the trialkylstannate anion yields allylic alcohols by anti elimination of the carbon halogen and adjacent carbon epoxy oxygen bonds. Appreciable Z→ E isomerization occurs in both types of reactions but the experimental results indicate that the conversion of erythro α-bromoepoxides to E allylic alcohols by zinc or trialkylstannates shows sufficient stereospecificity to be synthetically ...