Abstract
The purely organocatalyzed direct Michael addition of cycloalkanones to 1,3-diene-1,1-dicarboxylates was effected by a combination of (S)-2-(4-toluenesulfonamidomethyl)pyrrolidine and acetic acid. Addition products were formed in high yield and with good regio-, diastereo-, and enantioselectivity. The catalysis took place through a dual activation mode, that is, a nucleophilic enamine activation of the donor ketone and an eletrophilic hydrogen-bonding activation of the acceptor diene dicarboxylate. The addition products could easily undergo a stereoselective ketone reduction and subsequent lactonization to give compounds with high synthetic potential.
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