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 “donor” and the alkene (*) “acceptor” of this reaction are stabilized by resonance and contain one or more electron withdrawing groups. It’s not the aldol reaction, but a titanium tetrachloride catalyst is used with a silyl enol ether in this reaction’s Mukaiyama variant. This reaction has a similar mechanism to the Stork enamine reaction. This reaction begins the Robinson annulation. For 10 points, an enolate is joined to an alpha,beta-unsaturated carbonyl by what 1,4-addition reaction? ■END■
Summary
2024 Chicago Open | 07/28/2024 | Y | 15 | 93% | 0% | 20% | 118.14 |
Buzzes
Player | Team | Opponent | Buzz Position | Value |
---|---|---|---|---|
Kevin Wang | genAI this, genAI that, have you found your 真爱 yet | The Jeam Team | 59 | -5 |
Arya Karthik | Charlotte's Moderately Successful Team | Lying on a Mattress at Lou’s Apartment in Pilsen, Chicago | 79 | 10 |
Eric Mukherjee | LMM's LLM MLM | Punished "Venom" BHSU | 100 | 10 |
Billy Busse | BHSU B | The Empire Bikes Back | 107 | 10 |
Michael Hunding | SAYYID QUTB, DRIVING THE LONGEST CAR YOU’VE EVER SEEN THROUGH TAHRIR SQUARE | NJTRANSit (and anwen, I guess) | 111 | 10 |
Adam Fine | sticking out your guyot for the ridge push; you're so seafloor spread, you're so fracture zone | I’ll take a quiet 10 / A handshake of CO (Chicago Open) | 114 | 10 |
Iain Carpenter | Are You There, Chat? It's Me, Margaret | There are buzzable clues everywhere for those with eyes to see | 118 | -5 |
Richard Niu | AMOGH QUIZ HACK? 英雄联盟 400 PPG 24 TUH | Read slowly: A A A A A A A A A A A A A A A Read quickly: A | 118 | 10 |
Caleb Kendrick | We Need New Names | The Dyatlov Passement incident | 118 | 10 |
Vincent Du | A Nervy Liberal Nanny Hence | it's the great pumpkinification objection, charlie brown | 118 | 10 |
Kevin Ye | Berkeley Mafia and the Chicago Boy | Les Missourables | 121 | 10 |
Ryan Westbrook | when you look this good, you don’t have to know anything | First Cause, First Cause, make me young! | 129 | -5 |
Ethan Ashbrook | Galvanized Square Steen and Eco-Friendly Wood Vermeer | NJTRANSit (and bobby, i guess) | 132 | 10 |
Daniel Ma | There are buzzable clues everywhere for those with eyes to see | Are You There, Chat? It's Me, Margaret | 134 | 10 |
Mike Cheyne | The Oldest Men in the World | Lisan al-Quib | 134 | 10 |
Rohan Kher | var merchants | Mindgoblin of Little Hobbes | 134 | 0 |
Jason Hong | The Jeam Team | genAI this, genAI that, have you found your 真爱 yet | 134 | 10 |
Walter Zhang | Mindgoblin of Little Hobbes | var merchants | 134 | 10 |
Aidan Mehigan | First Cause, First Cause, make me young! | when you look this good, you don’t have to know anything | 134 | 0 |