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Intramolecular Baylis−Hillman and Morita Reactions Using Unsaturated Thiol Ester Substrates Containing Enolizable Aldehydes

2002; American Chemical Society; Volume: 4; Issue: 21 Linguagem: Inglês

10.1021/ol026638s

1523-7060

Gary E. Keck, Dennie S. Welch,

Synthesis and Reactivity of Sulfur-Containing Compounds

Previously unknown intramolecular Baylis−Hillman and Morita reactions involving cyclization of an unsaturated thiol ester onto a pendant aldehyde function are reported. These can be used successfully for the preparation of both cyclopentenols and cyclohexenols, but the results are very sensitive to substrate and precise reaction conditions.