CuH-catalyzed stereoselective desymmetrization of prochiral cyclopentane-1,3-diones via alkoxyallylation
Sundaram Maurya1,2, Vaibhav B Patil1, G Raghu Ramudu1,2
1Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India. rchegondi@iict.res.in.
Abstract:
We report a CuH-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted cyclopentane-1,3-diones through reductive alkoxyallylation. This strategy exploits the carbonyl group, an underexplored reactivity mode for the desymmetrization of cyclopentane-1,3-diones, constructing complex chiral carbocycles from simple symmetric diketones. This efficient, atom-economic transformation delivers functionalized cyclopentanones, bearing three consecutive stereocenters, including two quaternary carbons in a single operation. The protocol exhibits broad substrate scope, high diastereoselectivity, and moderate to good enantioselectivity.
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