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Synthesis of Chiral Tetrahydrofurans by a Palladium-Catalyzed Cycloaddition
B. M. Trost*, D. A. Bringley, S. M. Silverman
Stanford University, USA
20 July 2011 (online)
Tetrahydrofurans are simple heterocycles found in many natural and synthetic products. It has been previously demonstrated that chiral phosphoramidite ligands can induce enantio-selectivity in many trimethylenemethane (TMM) cycloadditions; however, the synthesis of tetrahydrofurans from aldehydes had proven to be difficult. The authors report the preparation of chiral methylenetetrahydrofurans by an enantioselective cycloaddition of aldehydes with TMM. The development of novel C 1-symmetric ligands was required, based on derivatization of the backbone of the BINOL component.