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Synlett 1996; 1996(12): 1203-1205
DOI: 10.1055/s-1996-5721
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Variable Stereoselectivity in the Imine Aldol Reactions Employing MgBr2 and Et3N

Kazuhiko Hayashi, Hiromi Kogiso, Shigeki Sano, Yoshimitsu Nagao*
  • *Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770, Japan
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Publication Date:
31 December 2000 (online)

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Imine aldol reactions of 1 and 2 employing 1.2 mol eq. of MgBr2 and 2.4 mol eq. of Et3N gave threo-excess products via a retro-imine aldol reaction at room temperature or erythro-excess products at -45 °C. The similar reactions employing 2.2 mol eq. of MgBr2 and 4.4 mol eq. of Et3N at room temperature afforded the threo-excess or erythro-excess products depending on the aldehydes 2.

Magnesium bromide - Metalloenamine - Stereoselection - Aldol reaction

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