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Synlett 1991; 1991(3): 173-175
DOI: 10.1055/s-1991-20667
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Enantioselective Deprotonation of Tropinone and Reactions of Tropinone Lithium Enolate

Marek Majewski* , Guo-Zhu Zheng
  • *Department of Chemistry, University of Saskatchewan, Saskatoon, Saskatchewan, Canada, S7N 0W0
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Publication Date:
07 March 2002 (online)

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Chiral lithium amide bases, e.g. lithium (R,R)-bis(1-phenylethyl)amide, deprotonate tropinone (8-methyl-8-azabicyclo[3.2.1]octan-3-one) and yield tropinone lithium enolate with modest enantioselectivity. The enolate reacts highly diastereoselectively with benzaldehyde producing the exo-anti aldol [2-(α-hydroxybenzyl)-8-methyl-8-azabicylco[3.2.1]octan-3-one].

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