Described is the design and preparation of chiral C2-symmetric malonamides and their application to asymmetric conjugate addition to enone. The mechanism of partial racemization observed in the course of hydrolysis–decarboxylation step is also elucidated.
Asymmetric bromolactonization reaction was found to proceed highly stereo- and regiospecifically via the transition state such as 5II when (S)-N-(α,β-unsaturated acyl)-α-amino acid, where two alkyl groups are located at the α and β positions in a cis relationship and free rotation of the bond between asymmetric carbon and nitrogen is prohibited due to cyclic structure, is used as a reaction substrate.
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