Green adaptations to known asymmetric aldol additions were investigated by replacing standard organic solvents with acidic, basic, and neutral Hot-Pressurized Water.  Spontaneous dehydrations to the enone were observed using proline as the chiral catalyst; however, stereoselectivity was very low.  Given the hydrophilic nature of proline, more hydrophobic amino acids were tested.  N-boc Alanine was evaluated as a catalyst in an attempt to mimic the secondary amine properties of proline.  Significant increases in stereoselectivity and overall yields of alcohol and enone mixed products were observed.

Cyclic asymmetric aldol additions and dehydrations in hot pressurized water

255th National Meeting (2018)

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