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ChemInform Abstract: Use of a Sulfinyl Tether to Control Diastereofacial Selectivity in (5C + 2C) Pyrone-Alkene Cycloadditions.

✍ Scribed by A. RUMBO; L. CASTEDO; J. L. MASCARENAS

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199746048

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✦ Synopsis

Use of a Sulfinyl Tether to Control Diastereofacial Selectivity in (5C + 2C) Pyrone-Alkene Cycloadditions.

-The incorporation of a sulfoxide group on the tether connecting an alkene to a 4-pyrone diminishes significantly the temperature needed for inducing their thermal (5C + 2C) cycloaddition compared to that required for cycloaddition of the homologous sulfide. Moreover, modest levels of diastereofacial selectivity are achieved.

Increasing the substitution at the sulfur further decreases the thermal requirements for the cycloaddition (cf. (IV) → (V)). -(RUMBO, A.; CASTEDO,

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