D.A. Evans Enolates Metalloenamines-2 Chem 206 Assigned Journal Articles http:/www.courses.fasharvardedu/-chem206/ Structure and Reactivity of Lithium Enolates. From Pinacolone to Selective C-Alkylations of Peptides. Difficulties and Opportunities Chemistry 206 Afforded by Complex Structures D Seebach Angew. Chem. Int Ed Engl, 27, 1624(1983).(handout) Advanced organic Chemistry Stereoselective Alkylation Reactions of Chiral Metal Enolates D A. Evans Asymmetric Synthesis, 3, 1(1984).(handout) Lecture Number 23 Other Useful references Advances in Asymmetric Enolate Methodology"Arya, Qin, Tetrahedron 2000 Enolates metalloenamines-2 56.917-94 Recent Advances in Dianion Chemistry". C M. Thompson and D L C. Green Tetrahedron,47,4223(1991) The reactions of dianions of carbo tragnani and M. Yonashiro Synth thesis, 21 1982). ter Generation of Simple Enols in Solution". Capon, Guo, Kwok, Siddhanta, and Introduction and General trends Zucco Acc. Chem. Res 21, 121(1988) Enolate Alkylation: Electronic& Steric Control Elements Enolate Alkylation: Unusual Cases Keto-Enol Equilibrium Constants of Simple Monofunctional Aldehydes and Ketones in Aqueous Solution". Keeffe, Kresge, and Schepp JACS, 112, 4862 Chiral amide enolate (1990) Chiral Ester enolates Chiral Imide enolates pKa and Keto-Enol Equilibrium Constant of Acetone in Aqueous Solution Chiral metalloenamines Chiang, Kresge, and Tang JACS 106, 460(1984) a Reading Assignment for this Week Carey& Sundberg: Part A; Chapter 7 Carbanions Other Nucleophilic Carbon Species Explain why A is favored for X =O while B is favored for X= NNHR Carey Sundberg: Part B; Chapter 2 ase Reactions of Carbon Nucleophiles with Carbonyl Compounds Matthew d shair Monday, November 11. 2002http://www.courses.fas.harvard.edu/~chem206/ R R O M R R N M R X Me Me A X Me Me B D. A. Evans Chem 206 Matthew D. Shair Monday, November 11, 2002 ■ Reading Assignment for this Week: Carey & Sundberg: Part A; Chapter 7 Carbanions & Other Nucleophilic Carbon Species Enolates & Metalloenamines-2 Carey & Sundberg: Part B; Chapter 2 Reactions of Carbon Nucleophiles with Carbonyl Compounds ■ Assigned Journal Articles Chemistry 206 Advanced Organic Chemistry Lecture Number 23 Enolates & Metalloenamines-2 "Structure and Reactivity of Lithium Enolates. From Pinacolone to Selective C-Alkylations of Peptides. Difficulties and Opportunities Afforded by Complex Structures". D. Seebach Angew. Chem. Int. Ed. Engl., 27, 1624 (1983). (handout) "Stereoselective Alkylation Reactions of Chiral Metal Enolates". D. A. Evans Asymmetric Synthesis, 3, 1 (1984). (handout) ■ Other Useful References "Advances in Asymmetric Enolate Methodology" Arya, Qin, Tetrahedron 2000, 56, 917-947 (pdf) "Recent Advances in Dianion Chemistry". C. M. Thompson and D. L. C. Green Tetrahedron, 47, 4223 (1991). The Reactions of Dianions of Carboxylic Acids and Ester Enolates". N. Petragnani and M. Yonashiro Synthesis, 521 (1982). "Generation of Simple Enols in Solution". Capon, Guo, Kwok, Siddhanta, and Zucco Acc. Chem. Res. 21, 121 (1988). "Keto-Enol Equilibrium Constants of Simple Monofunctional Aldehydes and Ketones in Aqueous Solution". Keeffe, Kresge, and Schepp JACS, 112, 4862 (1990). "pKa and Keto-Enol Equilibrium Constant of Acetone in Aqueous Solution". Chiang, Kresge, and Tang JACS 106, 460 (1984). ■ Introduction and General Trends ■ Enolate Alkylation: Electronic & Steric Control Elements ■ Enolate Alkylation: Unusual Cases ■ Chiral Amide Enolates ■ Chiral Ester Enolates ■ Chiral Imide Enolates ■ Chiral Metalloenamines Explain why A is favored for X = O while B is favored for X = NNHR base