Tetrahedron letters

Tin (II) chloride catalyzed addition of diazo sulfones, diazo phosphine oxides, and diazo phosphonates to aldehydes.

CR Holmquist, EJ Roskamp

Index: Holmquist, Christopher R.; Roskamp, Eric J. Tetrahedron Letters, 1992 , vol. 33, # 9 p. 1131 - 1134

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Citation Number: 74

Abstract

Abstract Diazo sulfones, diazo phosphine oxides, and diazo phosphonates add to aldehydes in the presence of a catalytic amounts of tin (II) chloride to yield β-keto sulfones, β- keto phosphine oxides, and β-keto phosphonates, respectively. Reactions with primary aldehydes proceed in higher yields, 53–79%, than those of secondary aldehydes, 42–56%. Reactions with tertiary aldehydes, which are more sterically encumbered substrates, give ...