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Synthesis 1994; 1994(5): 526-532
DOI: 10.1055/s-1994-25517
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A New Optically Active Monodentate Phosphine Ligand, (R)-(+)-3-Diphenylphosphino-3′-methoxy-4,4′-biphenanthryl (MOP-phen): Preparation and Use for Palladium-Catalyzed Asymmetric Reduction of Allylic Esters with Formic Acid

Tamio Hayashi* , Hiroshi Iwamura, Yasuhiro Uozumi, Yonetatsu Matsumoto, Fumiyuki Ozawa
  • *Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 060, Japan
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Publication Date:
17 September 2002 (online)

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(R)-(+)-3-Diphenylphosphino-3′-methoxy-4,4′-biphenanthryl (MOP-phen, 8) was prepared starting with (-)-3,3′-dihydroxy-4,4′-biphenanthryl. The absolute configuration of (+)-8 was determined to be R by X-ray crystal structure analysis of its π-allylpalladium complex. The monodentate optically active phosphine 8 was found to be a more enantioselective ligand than (R)-(+)-2-diphenylphosphino-2′-methoxy-1,1′-binaphthyl (MOP, 1a) for palladium-catalyzed asymmetric reduction of allylic esters with formic acid giving optically active olefins of up to 85% ee.