Enantioselective Deprotonation of Tropinone and Reactions of Tropinone Lithium Enolate
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (03) , 173-175
- https://doi.org/10.1055/s-1991-20667
Abstract
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].Keywords
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