Catalytic enantioselective reaction of diketene with aldehydes catalyzed by chiral Schiff base-titanium alkoxide complexes

Synlett

Volumn , Issue 6, 1998, Pages 601-602

  Oguni, Nobuku ^a   Tanaka, Kiyoshi ^a   Ishida, Hajime ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002441909     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1744     Document Type: Article

References (17)

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16. 4 (5.0 mmol) at room temperature and stirred for 1 h, then the mixture was cooled to -40°C. Freshly distilled aldehyde (5.0 mmol) and diketene (10.0 mmol) were added to it and the whole stored for 48 h at this temperature. The mixture was poured into a mixture of 1N HCl (50 mL) and diethyl ether (50 mL) and stirred for 2 h at room temperature. The mixture was then extracted with ethyl acetate (50 mL × 3), and the usual workup gave the product, (R)-5-hydroxy-3-oxoesters in good yield. The e.e. of the product was determined by HPLC analysis (Chiralpak AD) [eluent,hexane-ethanol (95:5) and trifluoroacetic acid (0.01%), 1.0 mL/min].
17. Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Lett. 1997, 38, 4351.