Rh-Catalyzed Desymmetric Hydroformylation of 1,3-Bis(methylene)cyclopentanes
Ting Ren1, Tianxiang Ren2, Cai You1
1Department of Chemistry, School of Sciences, Great Bay University, Dongguan 523000, People's Republic of China.
Abstract:
A highly enantio- and diastereoselective rhodium-catalyzed desymmetric hydroformylation of 1,3-bis(methylene)cyclopentanes has been developed using (R,R)-DTBM-YanPhos (up to 99% yield, 99% ee, and 50:1 dr), enabling access to chiral aldehydes bearing two contiguous stereocenters, including a quaternary center. The reaction proceeds under mild conditions and exhibits a broad substrate scope and functional group tolerance. Gram-scale synthesis and diverse downstream derivatizations demonstrate efficient access to densely substituted chiral cyclopentane derivatives and further expand the synthetic utility of desymmetric hydroformylation.
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