Tetrahedron Letters p. 1131 - 1134 (1992)
Update date:2022-08-03
Topics:
Holmquist, Christopher R.
Roskamp, Eric J.
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, 53-79percent, than those of secondary aldehydes, 42-56percent.Reactions with tertiary aldehydes, which are more sterically encumbered substrates, give only 5-36percent yields. KEY WORDS: Tin(II) chloride, catalyst, β-keto sulfones, β-keto phosphine oxides, and β-keto phosphonates.
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