D. A. Evans The aldol reaction -1 Chem 206 http:/www.courses.fas.harvardedu/-chem206/ ■ Assigned Reading Stereoselective Aldol Reactions in the Synthesis of Polyketic Products, I. Paterson et al. in Modern Carbonyl Chemistry, pp 249-297, J Chemistry 206 Otera, Ed. Wiley VCH, 2000 CCB Library Ager, D.J., L. Prakash, et al. (1997). "Chiral oxazolidinones in asymmetric Advanced Organic Chemistry synthesis. Aldrichimica Acta 30(1): 3-12 Other Useful References Lecture Number 24 Evans, D.A., J V. Nelson, et al. (1982). "Stereoselective Aldol Condensations The aldol reaction-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: 13 I Polyketide Biosynthesis Historical Perspective on the Aldol Reaction Heathcock, C. H(1991). The Aldol Reaction: Group I and Group lI Enolates Comprehensive Organic Synthesis. B M. Trost and L. Fleming. Oxford Aldol Diastereoselectivity Pergamon Press. 2: 181 nolate Diastereoface Selectivity Kim, B M, S. F Williams, et al. (1991). The Aldol Reaction: Group Ill Enolates Absolute control in the aldol process Comprehensive Organic Synthesis. B M. Trost and L. 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 Car anaes tner nrgc epah ic: capers Cowden, C J. and l. Paterson(1997). " Asymmetric aldol reactions using boron plates. o Carey& Sundberg: Part B: Chapter 2 Nelson, S.G.(1998). Catalyzed enantioselective aldol additions of latent Reactions of Carbon Nucleophiles with Carbonyl Compounds enolate equivalents. Tetrahedron: Asymmet Mahrwald, R.(1999). " Diastereoselection in Lewis-acid-mediated aldol Matthew d. shair Wednesday, additions. Chem. Rev. 99(5): 1095-1120 November 13 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 Wednesday, November 13, 2002 ■ Reading Assignment for this Week: Carey & Sundberg: Part A; Chapter 7 Carbanions & Other Nucleophilic Carbon Species The Aldol Reaction–1 Carey & Sundberg: Part B; Chapter 2 Reactions of Carbon Nucleophiles with Carbonyl Compounds Chemistry 206 Advanced Organic Chemistry Lecture Number 24 The Aldol Reaction–1 ■ Other Useful References ■ Polyketide Biosynthesis ■ Historical Perspective on the Aldol Reaction ■ Aldol Diastereoselectivity ■ Enolate Diastereoface Selectivity ■ Absolute Control in the Aldol Process 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. 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 CCB Library Ager, D. J., I. Prakash, et al. (1997). “Chiral oxazolidinones in asymmetric synthesis.” Aldrichimica Acta 30(1): 3-12 ■ Assigned Reading