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Tuesday, August 25 • 3:40pm - 4:00pm
[0080] Asymmetric Conjugate Addition of Alkylzirconocenes to Cyclopentene-3,5-dione Monoacetals

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Many methodologies have been developed in recent years but fail to address the challenges of cyclopentenones.2 Our group demonstrated that the conjugate addition of alkylzirconocenes to cyclohexenone derivatives is advantageous (Scheme 1a).3 However, when applying the methodology conditions to cyclopentenones, the yield was poor (23%) and the ee dropped (to 75%). Feringa et al. reported4 the derivatisation of cyclopentene-3,5-dione monoacetal 1 with diakylzinc reagents (Scheme 1b) in moderate yield (40%) and high ee (90%). The yield was significantly improved (to 69%) when trapping an aldehyde.

ST Lecturers
avatar for Emeline Rideau

Emeline Rideau

Graduate Student, University of Oxford



Tuesday August 25, 2015 3:40pm - 4:00pm
Girvetz 2116