Regiocontrolled and Stereocontrolled Diels-Alder Cycloadditions of 2-Pyrones and Unactivated, Unbranched 1-Alkenes

Gary H. Posner; Richard H. Hutchings; Benjamin T. Woodard

doi:10.1055/s-1997-6126

Synlett 1997; 1997(SI): 432-434
DOI: 10.1055/s-1997-6126

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Regiocontrolled and Stereocontrolled Diels-Alder Cycloadditions of 2-Pyrones and Unactivated, Unbranched 1-Alkenes

Gary H. Posner^* , Richard H. Hutchings, Benjamin T. Woodard

^*Department of Chemistry, The John Hopkins University, 3400 N.Charles Street, Baltimore, MD 21218, USA, Fax 410 516 8420; ghp@jhunix.hcf.jhu.edu

Abstract

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The combination of 10-12 kbar pressure plus a catalytic amount of either zinc dibromide or zinc dichloride promotes Diels-Alder cycloadditions of 3-bromo-2-pyrone and of commercial 3-methoxycarbonyl-2-pyrone with several unactivated terminal alkenes, leading regioselectively, stereoselectively and directly to versatile bicyclic lactones.

4+2 cycloadditions - 2-pyrones - unactivated alkenes - zinc dihalide catalyst

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