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A study of Lewis acid and hydrogen bond mediated soft enolization in the context of the Mannich reaction.
- Abstract:
We have shown that soft enolization of thioesters is an effective approach to the Mannich reaction. The size of the thiol component of the thioester was adjusted to influence the diastereoselectivity, and a chiral activator was used to produce enantioselectivity in the Mannich reaction. Two modes of soft enolization were explored: metal mediated and activation via hydrogen bonding. Both modes allow the -proton of a thioester to be deprotonated by a weak tertiary amine such as Hunig’s Base, something which typically requires much stronger bases and harsher reaction conditions. The magnesium mediated Mannich reaction produced a diasteromeric ratio of 5.3:1, and the chiral activator produced an enantiomeric ratio of 88:12, with a diasteromeric ratio of 98:2.
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