The Journal of Organic Chemistry

Synthesis of substituted pyridines via regiocontrolled [4+ 2] cycloadditions of oximinosulfonates

AR Renslo, RL Danheiser

Index: Renslo, Adam R.; Danheiser, Rick L. Journal of Organic Chemistry, 1998 , vol. 63, # 22 p. 7840 - 7850

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Citation Number: 68

Abstract

Diels-Alder cycloadditions of oximinosulfonate 8 with a variety of 1, 3-dienes proceed with regiochemistry opposite to that observed with conventional imino dienophiles, providing expeditious synthetic routes to substituted pyridines, tetrahydropyridines, and pyrrolines. The oximinosulfonate 8 is prepared in one convenient synthetic operation from Meldrum's acid and reacts with conjugated dienes at-78° C in the presence of 2 equiv of ...

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