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Organocatalytic Asymmetric Mannich Reaction of α-Alkynylated Cyclohexanones and Dione Counterparts With C-Alkynyl N-Boc N,O-Acetals: Access to 5/5/6 Tricyclic Frameworks
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DOI：10.1002/ajoc.70473.png)
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Abstract
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An enantioselective Mannich reaction of vinylogous carbonyl compounds with C-alkynyl N-Boc N,O-acetals has been developed. In the presence of a chiral phosphoric acid, β-aminocarbonyl products are obtained in good yields and up to 96% ee across a range of substrates. Use of a cyclohexanedione nucleophile leads to a marked rate enhancement, but lower enantioselectivity, which can be additionally improved with cinchona-derived hydrogen-bonding catalysts at elevated temperature. The products 6a, 6j, and 6g were further transformed into the 5/5/6 tricyclic frameworks via a Pauson–Khand reaction, highlighting their synthetic utility.
Keywords:
asymmetric synthesis
chiral phosphoric acid
cinchona-derived squaramide
enantioselective
Mannich reaction
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