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Synlett 2000; 2000(5): 0668-0670
DOI: 10.1055/s-2000-6639
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Mukaiyama Aldol Reaction of 1-Trimethylsilyloxy-1-cyclohexene with Benzaldehyde over Solid Superacids with Preferential Syn Selectivity

Hideo Nakamura* , Hiromi Matsuhashi, Kazushi Arata
  • *Department of Science, Hokkaido University of Education, Hachiman-cho, Hakodate 040-8567, Japan
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Publication Date:
31 December 2000 (online)

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The cross aldol reaction of 1-trimethylsilyloxy-1-cyclohexene with benzaldehyde over solid superacids of sulfated metal oxides (SO4/MeOx) and supported metal oxides (Me1Ox/Me2Ox) at 0 °C for 1 h afforded diastereoselectively aldols with preferential syn selectivity over SO4/TiO2, WO3/ZrO2, and WO3/TiO2 and anti selectivity over SO4/ZrO2; SO4/SnO2, SO4/Al2O3, and MoO3/ZrO2 have both products.

Mukaiyama aldol - solid superacids - syn - anti - trimethylsilyloxy-1-cyclohexene