Tetrahedron

Intermolecular 1, 3-dipolar cycloadditions of müchnones with acetylenic dipolarophiles: Sorting out the regioselectivity

BP Coppola, MC Noe, DJ Schwartz, RL Abdon…

Index: Coppola, Brian P.; Noe, Mark C.; Schwartz, David J.; Abdon II, Robert L.; Trost, Barry M. Tetrahedron, 1994 , vol. 50, # 1 p. 93 - 116

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Citation Number: 35

Abstract

A series of 1, 3-dipolar cycloadditions of münchnones with acetylenic dipolarophiles was studied, wherein factors related to regioselectivity were investigated. The results from münchnones with electronically divergent thioaryl substituents compared with others bearing alkyl substituents suggest that an unsymmetrical transition state structure, rather than FMO perturbation, plays a significant role in regioselection. If eclipsing interactions ...