Simon Lang Problem Set 1/25/13 - Department of Chemistry · Top JACS papers of 2012 “most...
Transcript of Simon Lang Problem Set 1/25/13 - Department of Chemistry · Top JACS papers of 2012 “most...
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Top JACS papers of 2012 “most downloaded over 12 months”
Simon Lang
Problem Set
1/25/13
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A New Method For Direct Difluoromethylation- Phil Baran JACS 2012 1494
• No prefunctionalization- direct transfer
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Mechanism?
DFMS = [Zn](SO2CF2H)2
TFA/solvent not used for mechanism Assume trace metal activates peroxide
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Mechanism?
PNAS 2011 14411-14415
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Rationalize these results
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(+)-Scholarisine A- Amos Smith III JACS 2012 4037
20 steps from known
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Provide the product
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Reductive Cyclization
Rxn name?
Draw/talk through what happens?
Benzoyl Chloride DMP
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Intermolecular Ritter-Type C-H Amination of Unactivated sp3 Carbons
• Phil Baran JACS 2547 2012
Inspiration
Reagent name??
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Mechanism?? Think: Selectfluor = electrophillic F and Ritter rxn
R. Eric Banks, Chem Comm 1996 1629.
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Nature-Inspired Total Synthesis of (-) Fusarisetin A
Emmanuel A. Theodorakis JACS 2012 5072 Nine steps from commercially available (S)-(-)-citronellal $20/g
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Get here first
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Via
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End Game
Mechanism???