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The Synthetic Utilization of 2-Hydroxymethyl-2,5-dihydrothiophene 1,1-Dioxide in the Intramolecular Diels-Alder Reaction

  • Published : 1994.06.20
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Abstract

2-Hydroxymethyl-2,5-dihydrothiophene 1,1-dioxide (1) was prepared from thiophene-2-carboxylic acid by consecutive reactions involving the Birch reduction, esterification, reduction with lithium aluminum hydride, and oxidation with Oxone$^{\circledR}$. The esterification of alcohol 1 with various unsaturated carboxylic acids provided the precursors 8 for the intramolecular Diels-Alder reaction. The cheletropic expulsion of sulfur dioxide from the esters 8 followed by intramolecular Diels-Alder reaction furnished bicyclic ${\gamma}$-and ${\delta}$-lactones.

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References

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Cited by

  1. ChemInform Abstract: The Synthetic Utilization of 2-Hydroxymethyl-2,5-dihydrothiophene 1,1- Dioxide in the Intramolecular Diels-Alder Reaction. vol.26, pp.8, 1994, https://doi.org/10.1002/chin.199508189
  2. Optimising Stereoselectivity in Intramolecular Diels–Alder Reactions of Pentadienyl Acrylates: Synthetic and Computational Investigations into the “Steric Directing Group” Approach vol.8, pp.3, 1994, https://doi.org/10.1002/1521-3765(20020201)8:3<739::aid-chem739>3.0.co;2-1