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Synlett 1997; 1997(SI): 455-456
DOI: 10.1055/s-1997-6152
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Preparation and Application of a Novel Type of Chiral Biphosphine Ligand (NORPHOS-7X) Containing a Hetero-Functional Group

Akira Yamazaki, Issei Achiwa, Kayoko Horikawa, Masue Tsurubo, Kazuo Achiwa*
  • *School of Pharmaceutical Science, University of Shizuoka, 52-1 Yada, Shizuoka 422, Japan
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Publication Date:
31 December 2000 (online)

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A new chiral biphosphine ligand containing a carboxyl group has been prepared by use of a silver-ion catalyzed rearrangement as a key step. And it has been applied to the rhodium-catalyzed asymmetric hydrogenation of the C=N double bond of N-benzoylhydrazone 12, for which on using (2R,3R,7S)-NORPHOS-7-COOH 1 containing a carboxyl group on the ligand, the opposite absolute configuration product 13 was observed as compared to using (2R,3R)-NORPHOS that has the same absolute configuration at the diphenylphosphino bearing carbons. This result showed the possibility of the interaction of the carboxyl group on the ligand with the substrate 12.

norphos-7X - chiral bisphosphine ligand - neighboring participation control

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