A Broadly Applicable NHC-Cu-Catalyzed Approach for Efficient, Site-, and Enantioselective Coupling of Readily Accessible (Pinacolato)alkenylboron Compounds to Allylic Phosphates and Applications to Natural Product Synthesis
Fang Gao, James L. Carr and Amir H. Hoveyda*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: amir.hoveydabc.edu
F. Gao, J. L. Carr, A. H. Hoveyda, J. Am. Chem. Soc., 2014, 136, 2149-2161.
DOI: 10.1021/ja4126565 (free Supporting Information)
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Enantioselective allylic additions of alkenyl units to readily accessible allylic electrophiles afford 1,4-dienes that contain a tertiary carbon stereogenic site in the presence of a copper complex of a chiral N-heterocyclic carbene (NHC). Aryl- as well as alkyl-substituted electrophiles bearing a di- or trisubstituted alkene may be employed. Reactions can involve a variety of robust alkenyl-(pinacolatoboron) compounds.
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