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Synlett 1995; 1995(4): 372-374
DOI: 10.1055/s-1995-4954
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Catalytic Enantioselective Protonation of Simple Enolate with Chiral Imide1

Akira Yanagisawa, Tetsuo Kikuchi, Tsuyoshi Watanabe, Takeshi Kuribayashi, Hisashi Yamamoto*
  • *School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
31 December 2000 (online)

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The catalytic enantioselective protonation of simple enolate was achieved using chiral proton source, (S,S)-imide 1 which possesses an asymmetric 2-oxazoline ring, as a catalyst. Treatment of the lithium enolate 4 with (S,S)-imide 1 (0.1 equiv) followed by addition of bulky phenol derivative or β-diketone as achiral proton source (1 equiv) afforded (R)-2,2,6-trimethylcyclohexanone (5) with high enantioselectivity.

Catalytic enantioselective protonation - Lithium enolate - Chiral imide - 2-Oxazoline - Achiral proton source