Question

This reaction occurs twice between a cuprate and an 8-membered enone ring in a total synthesis that starts with serine, whose namesake also modified this reaction. This reaction is the most common mechanism by which acrolein reacts with thiol groups on amino acids. An asymmetric example of this reaction attacks with 4-hydroxycoumarin to synthesize the anticoagulant Warfarin. Both the carbanion (-5[1])“donor” and the alkene (*) “acceptor” of this reaction are stabilized by resonance and contain one or more electron withdrawing groups. (10[1])It’s not the aldol reaction, but a titanium tetrachloride catalyst is used with a silyl enol ether in this reaction’s Mukaiyama (10[1])variant. This reaction has a similar mechanism (10[1])to the Stork enamine (10[1])reaction. This reaction (10[1])begins the Robinson annulation. (10[3]-5[1])For 10 points, (10[1])an enolate is joined to an alpha,beta-unsaturated carbonyl (-5[1])by what 1,4-addition (10[1])reaction? ■END■ (10[4]0[2])

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