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Synlett 1996; 1996(8): 796-798
DOI: 10.1055/s-1996-5519
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Enantioselective Synthesis of 2-Phosphino Alcohols via Phosphinylation of Metalated Chiral Aldehyde Hydrazones

Dieter Enders* , Thorsten Berg
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax: (int.)+ 241 8888 127; E-mail: Enders@RWTH-Aachen.de
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Publication Date:
31 December 2000 (online)

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A novel enantioselective access to 2-phosphino alcohols 5 via diastereoselective phosphinylation of chiral hydrazones 2 is described. After separation of the minor diastereomer, subsequent ozonolysis, reduction and removal of the borane protecting group the title compounds 5 are obtained in high enantiomeric purities (ee ≥ 96%).

2-phosphino alcohols - α-phosphino hydrazones - chiral hydrazones - asymmetric α-phosphinylation - phosphine-borane adducts