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Regioselective Crossed Aldol Reactions under Mild Conditions via Synergistic Gold-Iron Catalysis

Teng Yuan1, Xiaohan Ye1, Pengyi Zhao2

  • 1Department of Chemistry, University of South Florida, Tampa, FL, USA.

Chem
|January 22, 2024
PubMed

Keywords:
Aldol reactiongold catalysisiron catalysismacrocyclizationsynergistic catalysis

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This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
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