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Synfacts 2011(8): 0871-0871  
DOI: 10.1055/s-0030-1260739
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Tetrahydrofurans by a Palladium-Catalyzed Cycloaddition

Contributor(s): Mark Lautens, Stephen G. Newman
B. M. Trost*, D. A. Bringley, S. M. Silverman
Stanford University, USA
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

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.