D.A. Evans Olefin Addition Reactions: Part-2 Chem 206 Other Reading Material http://www.courses.fasharvard.edu/-chem206/ Takaya, H, T. Ohta, et al. (1993). Asymmetric Hydrogenation Catalytic Asymmetric Synthesis. L Ojima. New York, VCH: 1-39 Chemistry 206 Bolm, C (1993)." Enantioselective transition metal-catalyzed hydrogenation for the asymmetric synthesis of amines. Angew. Chem., Int. Ed Engl. 32: 232 Advanced Organic Chemistry For a recent general review of the Simmons-Smith reaction see Lecture number 9 Charette& Beauchemin, Organic Reactions, 58, 1-415(2001) Problems of the Day: (To be discussed Olefin Addition reactions-2 Epoxidation& Directed Epoxidation Predict the stereochemical outcome of the indicated reaction Hydrogenation Hydride Reduction L2, NaHCO3 Reading Assignment for week Kinetic Control: 3 eq I2, MeCN, NaHCO3, 0-C A. Carey Sundberg: Part B; Chapter 4 diastereoselection: 20: 1 Electrophilic Additions to C-C Multilple Bonds Bartlett, P. A; Richardson, D. Myerson, J. Tetrahedron 1984, 12, 2317 K.Houk, Science.1986,231,1108-1117 Theory Modeling of Stereoselective Organic Reactions(Handout) Rationalize the stereochemical outcome of the indicated reaction Houk. Tetrahedron. 1984. 40. 2257-2274 Theoretical Studies of stereoselective Hydroboration Reactions Hoveyda, Evans, Fu(1993). Substrate-directable chemical reactions. Chem. Rev. 93: 1307-70(Handout) Monday, Matthew d shair October 7. 2002 Bull. Chem. Soc. Japan 47, 2617, (1974) LiAIH4http://www.courses.fas.harvard.edu/~chem206/ Me Me HOOC Me I2, NaHCO3 N Me O OH N M–H Me H LiAlH4 R2AlH O O Me Me Me I N Me H OH D. A. Evans Chem 206 Matthew D. Shair Monday, October 7, 2002 ■ Reading Assignment for week A. Carey & Sundberg: Part B; Chapter 4 "Electrophilic Additions to C–C Multilple Bonds" Olefin Addition Reactions: Part–2 Chemistry 206 Advanced Organic Chemistry Lecture Number 9 Olefin Addition Reactions–2 K. Houk, Science. 1986, 231, 1108-1117 Theory & Modeling of Stereoselective Organic Reactions (Handout) ■ Epoxidation & Directed Epoxidation ■ Hydrogenation ■ Hydride Reduction K. Houk, Tetrahedron. 1984, 40, 2257-2274 Theoretical Studies of Stereoselective Hydroboration Reactions (Handout) Hoveyda, Evans, & Fu (1993). Substrate-directable chemical reactions. Chem. Rev. 93: 1307-70 (Handout) ■ Problems of the Day: (To be discussed) ■ Other Reading Material Takaya, H., T. Ohta, et al. (1993). Asymmetric Hydrogenation. Catalytic Asymmetric Synthesis. I. Ojima. New York, VCH: 1-39. Bolm, C. (1993). “Enantioselective transition metal-catalyzed hydrogenation for the asymmetric synthesis of amines.” Angew. Chem., Int. Ed. Engl. 32: 232. diastereoselection: 20:1 Predict the stereochemical outcome of the indicated reaction. Bartlett, P. A.; Richardson, D.; Myerson, J. Tetrahedron 1984, 12, 2317 Kinetic Control: 3 eq. I2 , MeCN, NaHCO3 , 0°C R. Noyori Bull. Chem. Soc. Japan 47, 2617, (1974) 28 : 72 97 : 3 Rationalize the stereochemical outcome of the indicated reaction. For a recent general review of the Simmons-Smith reaction see: Charette & Beauchemin, Organic Reactions, 58, 1-415 (2001)