D. A. Evans Cycloaddition Reactions: Part-1 Chem 206 Other Reading material http://www.courses.fas.harvardedu/-chem206/ [2+2] Cycloaddition Reactions Tidwell, T. T. Ketenes, John Wiley and Sons, 1995 Chemistry 206 Ghosez, L; Marchand-Brynaert, J. Comprehensive Organic Synthesis, Vol 5, Pergamon, 1991, p. 85-122 Advanced Organic Chemistry The Diels-Alder Cycloaddition Reactions Diels-Alder Reactions". Evans. D. A: Johnson J. s In Lecture number 15 Comprehensive Asymmetric Catalysis, Jacobsen, E N; Pfaltz, A and yamamoto, h ed oringer Verlag: Heidelberg, 1999: Vol ll.1178-1235(pdf Cycloaddition Reactions-1 ■ Problems of the Day I Introduction to Cycloaddition Reactions Propose a mechanism for this transformation I(2+2] Cycloaddition Reactions The Diels- Alder reaction EtN(Pr)2 Reading Assignment for week Carey Sundberg: Part A; Chapter 11 Concerted Pericyclic Reactions MacMillan, JACS 1999. 121 9726 Carey Sundberg: Part B; Chapter 6 Cycloadditions, Unimolecular Rearrangements Thermal eliminations Predict the stereochemical outcome of this reaction Fleming: Chapter 4 2 LDA, TMSCI oH O Thermal Pericyclic Reactions Wednesday Matthew d. shair October 23 2002 Kut,JOc1985,50,1840http://www.courses.fas.harvard.edu/~chem206/ O N Me Cl Me O TiCl4 Me O OH O Me O N O Me Me OH O Me OTMS Me D. A. Evans Chem 206 Matthew D. Shair Wednesday, October 23, 2002 ■ Reading Assignment for week: Carey & Sundberg: Part A; Chapter 11 Concerted Pericyclic Reactions Cycloaddition Reactions: Part–1 Chemistry 206 Advanced Organic Chemistry Lecture Number 15 Cycloaddition Reactions-1 ■ Introduction to Cycloaddition Reactions ■ [2+2] Cycloaddition Reactions ■ The Diels-Alder Reaction ■ Other Reading Material: Fleming: Chapter 4 Thermal Pericyclic Reactions ■ Problems of the Day: [2+2] Cycloaddiltion Reactions The Diels-Alder Cycloaddition Reactions EtN(iPr)2 Propose a mechanism for this transformation MacMillan, JACS 1999, 121, 9726 Carey & Sundberg: Part B; Chapter 6 Cycloadditions, Unimolecular Rearrangements Thermal Eliminations Tidwell, T. T. Ketenes, John Wiley and Sons, 1995. Ghosez, L.; Marchand-Brynaert, J. Comprehensive Organic Synthesis, Vol. 5, Pergamon, 1991, p. 85-122. "Diels-Alder Reactions". Evans, D. A.; Johnson J. S. In Comprehensive Asymmetric Catalysis, Jacobsen, E. N.; Pfaltz, A.; and Yamamoto, H. Editors; Springer Verlag: Heidelberg, 1999; Vol III, 1178-1235 (pdf) 2 LDA, TMSCl ❉ ❉ Kurth, JOC 1985, 50, 1840 Predict the stereochemical outcome of this reaction