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UD CHEM 634 - Lecture notes

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• Enolate formation: Kinetic vs. Thermodynamic controlEvans, D. A. Stereoselective Alkylation Reactions of Chiral Metal Enolates.In Asymmetric Synthesis. Stereodifferentiating Reactions, Part B.;Morrison, J. D., Ed.; AP: New York, 1984; Vol. 3, p 1.• Stereocontrolled formation of enolatesIreland, R. E.; Mueller, R. H.; Willard, A. K. The ester enolate Claisenrearrangement. Stereochemical control through stereoselective enolateformation. J. Am. Chem. Soc. 1976, 98, 2868–2877.Ireland, R. E.; Wipf, P.; Joseph D. Armstrong, III Stereochemical control inthe ester enolate Claisen rearrangement. 1. Stereoselectivity in silylketene acetal formation. J. Org. Chem. 1991, 56, 650-657.A-1,3 strain as a control element in enolate alkylationsFleming Chem. Commun. 1985 318Fleming Chem. Commun. 1984 904• Stereocontroled alkylation of endocyclic enolatesEvans, D. A. Stereoselective Alkylation Reactions of Chiral Metal Enolates.In Asymmetric Synthesis. Stereodifferentiating Reactions, Part B.;Morrison, J. D., Ed.; AP: New York, 1984; Vol. 3, p 1.• Stereocontroled alkylation of exocyclic enolatesEvans, D. A. Stereoselective Alkylation Reactions of Chiral Metal Enolates.In Asymmetric Synthesis. Stereodifferentiating Reactions, Part B.;Morrison, J. D., Ed.; AP: New York, 1984; Vol. 3, p 1.Krapcho, A. P.; Dundulis, E. A. Stereochemistry of alkylation of carboxylicacid salt and ester .alpha. anions derived from cyclic systems. J. Org.Chem. 1980, 45, 3236-3245.• Aldehyde alkylationGroenewegen, et al Tetrahedron Lett. 1978, 494.• Synthesis of B-ketoesters by acylation with Mander’s reagentMander, Tetrahedron Lett. 1983, 24, 5425• Alkylation of B-ketoester dianionsHuckin, S. N.; Weiler, L. Alkylation of dianions of .beta.-keto esters. J. Am.Chem. Soc. 1974, 96, 1082-1087.• Enolates by reduction of enonesStork, G.; Rosen, P.; Goldman, N.; Coombs, R. V.; Tsuji, J. Alkylation andCarbonation of Ketones by Trapping the Enolates from the Reduction of ,-Unsaturated Ketones. J. Am. Chem. Soc. 1965, 87, 275-286.Caine et. Al. Org. Syn. CV 6, 51.•!Alkylations of MetalloiminesHosomi, A.; Araki, Y.; Sakurai, H. Remarkably high regioselectivedeprotonation and alkylation of unsymmetrical imines at the moresubstituted .alpha.-carbon atom. J. Am. Chem. Soc. 1982, 104, 2081-2083.Stork, G.; Dowd, S. R. A New Method for the Alkylation of Ketones andAldehydes: the C-Alkylation of the Magnesium Salts of N-SubstitutedImines. J. Am. Chem. Soc. 1963, 85, 2178-2180.Martin, S. F. Metalloenamines. In Comprehensive Organic Synthesis; Trost,B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 475.Liao and Collum, J. Am. Chem. Soc. 2003, 125, 15114.•!Alkylations of Extended enolatesCargill, R. L.; Bushey, D. F.; Good, J. J. Alkylation of 1-cyanocyclohexene.J. Org. Chem. 1979, 44, 300-301.• Claisen Rearrangements: ReviewsWipf, P. Claisen Rearrangements. In Comprehensive Organic Synthesis;Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p827.Rhoads, S. J.; Raulins, N. R. The Claisen and Cope Rearrangements. Org.React. (N.Y.) 1975, 22, 1.• Chirality Transfer in Claisen RearrangementsHill, R. K. Chirality Transfer via Sigmatropic Rearrangements. InAsymmetric Synthesis. Stereodifferentiating Reactions, Part A.; Morrison,J. D., Ed.; AP: New York, 1984; Vol. 3, p 502.• Ireland ClaisenChai, Y.; Hong, S.-p.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. Newaspects of the Ireland and related Claisen rearrangements. Tetrahedron2002, 58, 2905-2928.reland, R. E.; Mueller, R. H.; Willard, A. K. The ester enolate Claisenrearrangement. Stereochemical control through stereoselective enolateformation. J. Am. Chem. Soc. 1976, 98,


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