Catalytic Asymmetric Iodocarbocyclization Reaction of 4-Alkenylmalonates and Its Application to Enantiotopic Group Selective Reaction

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Abstract
The iodocarbocyclization reaction of 4-alkenylmalonate derivatives proceeded with excellent enantioselectivity (≥95% ee) in the presence of 10−40 mol % of Ti(TADDOLate)2. The Ti(TADDOLate)2-mediated catalytic asymmetric reaction was extended to the enantiotopic group selective reaction of bisalkenylated malonates, giving rise to trisubstituted cyclopentanoid compounds with both high diastereoselectivity (86−94% de) and excellent enantioselectivity (≥95% ee). An efficient synthesis of (+)-boschnialactone from the product of the present reaction was also achieved.

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