D. A. Evans The aldol reaction -2 Chem 206 http:/www.courses.fasharvardedu/-chem206/ ■ Assigned Reading Stereoselective Aldol Reactionsw in the Synthesis of Polyketide natural Products, I. Paterson et al. in Modern Carbonyl Chemistry, pp 249-297, J Chemistry 206 Otera, Ed. Wiley VCH, 2000(handout) W.R. Roush, J. Org. Chem. 1991, 56, 4151-4157.(handout Advanced Organic Chemistry Other Useful References Lecture Number 25 Evans, D.A., J V. Nelson, et al. (1982). "Stereoselective Aldol Condensation Top. Stereochem. 13: 1 The aldol reaction-2 Heathcock, C H (1984). The Aldol Addition Reaction. Asymmetric Synthesis Stereodifferentiating Reactions, Part B J D. Morrison. New York, AP. 3: 111 Oppolzer, W.(1987). "Camphor Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. Tetrahedron 43: 1969 Heathcock, C. H (1991). The Aldol Reaction: Acid and General Base Catalysis Comprehensive Organic Synthesis. B M. Trost and L. Fleming. Oxford Pergamon Press. 2: 133 ■&团 Enolates: Felkin Selectivity Heathcock, C. H (1991). The Aldol Reaction: Group I and Group ll Enolate a Double Stereodifferentiating Aldol Reactions Comprehensive Organic Synthesis. B M. Trost and L. Fleming. Oxford The Mukaiyama Aldol Reaction Variant Pergamon Press. 2: 181 Allylmetal Nucleophiles as Enolate Synthons Kim, B M, S. F Williams, et al. (1991). The Aldol Reaction Group Ill Enolates Comprehensive Organic Synthesis. B M. Trost and I Fleming. Oxford Pergamon Press. 2: 239 a Reading Assignment for this Week Franklin, A. S and L. Paterson(1994). "Recent Developments in Asymmetric Aldol meth y. Contemporary Organic Synthesis 1: 317-338 Carey Sundberg: Part A; Chapter 7 Cowden, C J and l. Paterson(1997).". etric aldol reactions using boron Carbanions Other Nucleophilic Carbon Species enolates. Org. React (N.Y. ) 51: 1-200 Carey Sundberg: Part B: Chapter 2 Nelson, S G (1998). Catalyzed enantioselective aldol additions of late Reactions of Carbon Nucleophiles with Carbonyl Compounds enolate equivalents. " Tetrahedron: Asymmetry 9(3): 357-389 Mahrwald, R (1999). "Diastereoselection in Lewis-acid-mediated aldol Matthew d. shair additions. Chem. Rev. 99(5): 1095-1120 November 15. 2002http://www.courses.fas.harvard.edu/~chem206/ R Me O M O H R R R O Me O M D. A. Evans Chem 206 Matthew D. Shair Friday, November 15, 2002 ■ Reading Assignment for this Week: Carey & Sundberg: Part A; Chapter 7 Carbanions & Other Nucleophilic Carbon Species The Aldol Reaction–2 Carey & Sundberg: Part B; Chapter 2 Reactions of Carbon Nucleophiles with Carbonyl Compounds Chemistry 206 Advanced Organic Chemistry Lecture Number 25 The Aldol Reaction–2 ■ Other Useful References ■ (E) & (Z) Enolates: Felkin Selectivity ■ Double Stereodifferentiating Aldol Reactions ■ The Mukaiyama Aldol Reaction Variant ■ Allylmetal Nucleophiles as Enolate Synthons Evans, D. A., J. V. Nelson, et al. (1982). “Stereoselective Aldol Condensations.” Top. Stereochem. 13: 1. Heathcock, C. H. (1984). The Aldol Addition Reaction. Asymmetric Synthesis. Stereodifferentiating Reactions, Part B. J. D. Morrison. New York, AP. 3: 111. Oppolzer, W. (1987). “Camphor Derivatives as Chiral Auxiliaries in Asymmetric Synthesis.” Tetrahedron 43: 1969. Heathcock, C. H. (1991). The Aldol Reaction: Acid and General Base Catalysis. Comprehensive Organic Synthesis. B. M. Trost and I. Fleming. Oxford, Pergamon Press. 2: 133. Heathcock, C. H. (1991). The Aldol Reaction: Group I and Group II Enolates. Comprehensive Organic Synthesis. B. M. Trost and I. Fleming. Oxford, Pergamon Press. 2: 181. Kim, B. M., S. F. Williams, et al. (1991). The Aldol Reaction: Group III Enolates. Comprehensive Organic Synthesis. B. M. Trost and I. Fleming. Oxford, Pergamon Press. 2: 239. Franklin, A. S. and I. Paterson (1994). “Recent Developments in Asymmetric Aldol Methodology.” Contemporary Organic Synthesis 1: 317-338. Cowden, C. J. and I. Paterson (1997). “Asymmetric aldol reactions using boron enolates.” Org. React. (N.Y.) 51: 1-200. Nelson, S. G. (1998). “Catalyzed enantioselective aldol additions of latent enolate equivalents.” Tetrahedron: Asymmetry 9(3): 357-389. Mahrwald, R. (1999). “Diastereoselection in Lewis-acid-mediated aldol additions.” Chem. Rev. 99(5): 1095-1120. ■ Assigned Reading Stereoselective Aldol Reactionsw in the Synthesis of Polyketide natural Products, I. Paterson et al. in Modern Carbonyl Chemistry, pp 249-297, J. Otera, Ed. Wiley VCH, 2000 (handout) W. R. Roush, J. Org. Chem. 1991, 56, 4151-4157. (handout)