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Radical Cyclization/β-Elimination Tandem Reactions: Enantiopure Sulfoxides as Temporary Chiral Auxiliaries

✍ Scribed by Emmanuel Lacôte; Bénédicte Delouvrié; Louis Fensterbank; Max Malacria

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 109 KB
Volume: 37
Category: Article
ISSN: 0044-8249
DOI: 10.1002/(sici)1521-3773(19980817)37:15<2116::aid-anie2116>3.0.co;2-l

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✦ Synopsis

Alkylidene-substituted cyclopentane derivatives are formed in high enantiomeric purity by the reaction shown below. A highly diastereoselective radical cyclization is followed by elimination of a β-sulfinyl radical. Interestingly, the addition of the Lewis acid methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) totally reverses the stereochemical outcome of the reaction. E=CO Me.

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