Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species
Dr. Won Jun Jang
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419 Korea
Search for more papers by this authorJeongkyu Woo
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419 Korea
Search for more papers by this authorCorresponding Author
Prof. Jaesook Yun
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419 Korea
Search for more papers by this authorDr. Won Jun Jang
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419 Korea
Search for more papers by this authorJeongkyu Woo
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419 Korea
Search for more papers by this authorCorresponding Author
Prof. Jaesook Yun
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon, 16419 Korea
Search for more papers by this authorAbstract
We report the diastereo- and enantioselective conjugate addition of chiral secondary borylalkyl copper species derived from borylalkenes in situ to α,β-unsaturated diesters. In the presence of a chiral bisphosphine-ligated CuH catalyst, the conjugate addition provides a direct access to enantioenriched alkylboron compounds containing two contiguous carbon stereogenic centers in good yield with high diastereo- and enantioselectivity (up to >98:2 dr, >99:1 er) by assembling readily available starting alkenyl reagents in a single operation without using preformed organometallic reagents or chiral auxiliaries. The resulting products were used in various organic transformations. The utility of the synthetic approach was highlighted by the synthesis of (−)-phaseolinic acid.
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