STEREOSPECIFICITY OF THE REACTION OF (+)-(4S,5S)-4-(4-NITROPHENYL)-1-AZA-3,7-DIOXABICYCLO[3.3.0]OCTANE WITH METHYL IODIDE

Abstract

The MINDO3, MNDO, AM1, and PM3 methods have been used to optimize the geometries of (+)-(4S,5S)-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octane and (+)-(4S,5S)-4-phenyl-1-aza-3,7-dioxabicyclo[3.3.0]octane. It has been shown that the stereospecificity of the reaction of the former with methyl iodide is due to the high stability of one of the possible conformers.

Authors: J. Couquelet, M. Madesclaire, F. Leal, V. P. Zaitsev, and S. Kh. Sharipova.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (10), pp 1242-1244

http://link.springer.com/article/10.1007/BF02323386