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Synlett 1998; 1998(4): 437-439
DOI: 10.1055/s-1998-1677
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Enantio- and Diastereoselective Synthesis of anti-α-Bromo-α-fluoro-β-hydroxycarbonylates

Katsuhiko Iseki* , Yoshichika Kuroki, Yoshiro Kobayashi
  • *MEC Laboratory, Daikin Industries, Ltd., Miyukigaoka, Tsukuba, Ibaraki 305, Japan; Fax + 81-298-58-50 82; E-mail: iseki@mec.daikin.co.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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Reaction of aldehydes with bromofluoroketene silyl acetal 1 in the presence of 20 mol% chiral Lewis acid 2 proceeds with enantio- and diastereoselectivities at -20 °C to afford optically active anti-α-bromo-α-fluoro-β-hydroxy esters 3a-f (up to 89:11 anti:syn, up to 93% ee).

catalytic asymmetric aldol reaction - bromofluoroketene silyl acetal - chiral fluoroorganic compounds - α-bromo-α-fluoro-β-hydroxy esters - aldehyde