Palladium(II)-catalyzed 1,4-addition of arylboronic acids to β-arylenals for enantioselective syntheses of 3,3-diarylalkanals: a short synthesis of (+)-(R)-CDP 840 |
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| Authors: | Takashi Nishikata Norio Miyaura |
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| Institution: | a Innovation Plaza Hokkaido, Japan Science and Technology Agency, Sapporo 060-0819, Japan
b Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan |
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| Abstract: | 1,4-Addition of arylboronic acid to trans-β-arylenals proceeded smoothly in acetone-water (10/1) at 10-25 °C in the presence of Pd(S,S-chiraphos)(PhCN)2](SbF6)2 (0.5 mol %), AgX (X = BF4, SbF6, 10 mol %) and aqueous 42% HBF4 to afford optically active 3,3-diarylalkanals with high enantioselectivities in a range of 86-97% ee. The protocol provided a method for short-step synthesis of optically active (+)-(R)-CDP 840. |
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| Keywords: | Conjugate addition Asymmetric synthesis Asymmetric catalyst Arylboronic acid Chiral aldehydes |
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