Papers

2021 Papers for reading & in-class discussion

  1. (discuss M, Feb 8) J.R. Henderson et al., “Diastereoselective Diels-Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary,” OL, 2007, 5167 (DOI 10.1021/ol702280q) | Reading instructions (in HW#2)
  2. J.I. Brauman, W.C. Archie, Jr., “Energies of Alternate Electrocyclic Pathways. Pyrolysis of cis-3,4-Dimethylcyclobutene,” J. Am. Chem. Soc., 1972, 4262- 4265 (DOI 10.1021/ja00767a038) | Reading instructions & writing prompts (respond Su, Mar 14) | Alan responds to questions about experimental procedure (Mar 23)

2020 Papers for reading & in-class discussion

  1. (discuss W, Jan 29) R.E.K. Winter, “The Preparation and Isomerization of cis– and trans-3,4-Dimethylcyclobutene,” Tet. Lett., 1965, 1207-1212 (paywall: DOI 10.1016/S0040-4039(01)83997-6, contact me for copy) | Reading instructions & writing prompts | comments & answers
  2. (discuss W, Feb 19) J.I. Brauman, W.C. Archie, Jr., “Energies of Alternate Electrocyclic Pathways. Pyrolysis of cis-3,4-Dimethylcyclobutene,” J. Am. Chem. Soc., 1972, 4262- 4265 (DOI 10.1021/ja00767a038) | Reading instructions & writing prompts |Round #2 prompts
  3. (discuss W, Mar 4? OR F, Mar 6?) Iafe & Houk, “Stereoselectivity Control by Torsional Steering in an Intramolecular Diels-Alder Reaction of Vinyl Oxocarbenium Ions,” OL, 2006, 3469 (DOI 10.1021/ol061085x) | Reading Instructions || Glossary | TS7 | TS8 | TS9 | TS10 | TS11 | TS12 | TS13 | TS14 | instructions for converting published (xyz) models into Spartan models
  4. tba

2019 Papers for reading & in-class discussion

  1. (discuss F, Feb 1) R.E.K. Winter, “The Preparation and Isomerization of cis- and trans-3,4-Dimethylcyclobutene,” Tet. Lett., 1965, 1207-1212 (paywall: DOI 10.1016/S0040-4039(01)83997-6, contact me for copy) | Reading instructions & writing prompts
  2. (discuss W, Feb 13) J.R. Henderson et al., “Diastereoselective Diels-Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary,” OL, 2007, 5167 (DOI 10.1021/ol702280q) | Reading instructions for W
  3. (discuss F, Feb 22) Iafe & Houk, “Stereoselectivity Control by Torsional Steering in an Intramolecular Diels-Alder Reaction of Vinyl Oxocarbenium Ions,” OL, 2006, 3469 (DOI 10.1021/ol061085x) | Reading Instructions for F || Glossary | TS7 | TS8 | TS9 | TS10 | TS11 | TS12 | TS13 | TS14

2017 Sneaker Logs

  1. (discuss W, Jan 25) W. Scholz et al., “Crystal Structure Determination of the Nonclassical 2-Norbornyl Cation,” Science, 2013, 62-64 (DOI 10.11126/science.1238849) | Reading instructions for Wed

2015 Flotsam

  • (discuss W, Mar 4) – C.P. Casey et al., “Stereochemistry and Mechanism of the Ring-Opening Reaction of Cyclopropylenones with LiCu(Me)2,” Organomet., 2012, 7849 (DOI 10.1021/om300520r) | Reading Instructions
  • (discuss W, Mar 18) – P.P. Painter et al., “The Viability of Nitrone−Alkene (3 + 2) Cycloadditions in Alkaloid Biosynthesis,” JOC, 2014, 432 (DOI 10.1021/jo402487d) | Reading Instructions

2014 Jetsam

  1. (discuss 1st half, W, Feb 19) (discuss 2nd half, W, Feb 26) L.R. Domingo et al., “Understanding the Participation of Quadricyclane as Nucleophile in Polar [2σ + 2σ + 2π] Cycloadditions toward Electrophilic π Molecules,” JOC, 2008, 73, 8791 (DOI 10.1021/jo801575g) | Reading Instructions
  2. (discuss F, Apr 11) – Howard & Woerpel, “Synthesis of Tertiary α-Hydroxy Acids by Silylene Transfer to α-Keto Esters,” OL, 2007, 9, 4651 (DOI 10.1021/ol702148x) Reading Instructions
  3. (discuss M, Apr 21) – Hong & Tantillo, “Biosynthetic Consequences of Multiple Sequential Post-Transition-State Bifurcations,” Nature Chem., 2014, 6, 104-111 (DOI: 10.1038/nchem.1843) | Reading Instructions (Read this first: C&ENews summary (March 24, 2014, p. 34-5) “Dynamics Determine Enzyme Selectivity”
  4. Student-led discussion: Senior Ladies (discuss F, Apr 25) – Olson & Davies, “Asymmetric [4 + 3] Cycloadditions between Benzofuranyldiazoacetates and Dienes: Formal Synthesis of (+)-Frondosin B,” OL, 2008, 10(4), 573-576 (DOI 10.1021/ol702844g)
  5. Student-led discussion: Üm-Louts (discuss M, Apr 28) – A.R. Rivero et al., “Regio- and Diastereoselective Stepwise [8 + 3]-Cycloaddition Reaction between Tropone Derivatives and Donor–Acceptor Cyclopropanes,” OL, 2013, 15(19), 4928-4931 (DOI 10.1021/ol4020656)
  6. Student-led discussion: Gang of Four (discuss W, Apr 30) – J.A.R. Luft et al., “Transition Structures of Diastereoselective 1,3-Dipolar Cycloadditions of Nitrile Oxides to Chiral Homoallylic Alcohols,” OL, 2007, 9(4), 555-558 (DOI 10.1021/ol062751x)