One-Pot Synthesis of Chiral Spiro-Imidazolidinone Cyclohexenones
1Department of Chemistry, The Citadel, 171 Moultrie Street, Charleston, South Carolina 29409, United States.
Abstract:
We have developed a simple and straightforward synthesis of chiral spiro-imidazolidinone cyclohexenones, featuring six contiguous stereocenters, from feedstock chemicals such as aminophenols, α,β-unsaturated aldehydes, and α-amino acids. Remarkably, this one-pot multicomponent reaction exhibits exceptional diastereoselectivity (>20:1 dr) and relies solely on an amino acid precursor as the chiral source, avoiding the use of transition metals or additional organocatalysts. This reaction is efficient and scalable, enabling synthesis on a gram-scale.
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