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Extra info for Advanced Organic Chemistry, Part B: Reactions and Synthesis;
M. Harris and C. M. Harris, Org. React. , 17, one hundred fifty five (1969); E. M. Kaiser, J. D. Petty, and P. L. A. Knutson, Synthesis, 509 (1977); C. M. Thompson and D. L. C. eco-friendly, Tetrahedron, forty seven, 4223 (1991); C. M. Thompson, Dianion Chemistry in natural Synthesis, CRC Press, Boca Raton, FL, 1994. D. M. von Schriltz, okay. G. Hampton, and C. R. Hauser, J. Org. Chem. , 34, 2509 (1969). J. E. Baldwin and L. I. Kruse, J. Chem. Soc. , Chem. Commun. , 233 (1977). J. E. Baldwin, R. C. Thomas, L. I. Kruse, and L. Silberman, J. Org. Chem. , forty two, 3846 (1977). J. M. Conia and F. Rouessac, Tetrahedron, sixteen, forty five (1961). 37 Scheme 1. 7. iteration and Alkylation of Dianions O– O 1a CH3CCH2CHO 2b O KNH2 2 equiv O CH2 O– C CH C CH – CHOH KNH2 CH3 2 equiv CHO part 1. 2 O Alkylation of Enolates PhCH2CH2CCH2CHO eighty% O O 1) C4H9Br CH (CH ) CCH three 2 four 2CCH3 2) H3O+ CCH3 O– O CH3 2) H3O+ O– O– NaNH2 CH3CCH2CCH3 2 equiv CH2 3c CH 1) PhCH2Cl O CH3 C4H9Br CHO– CH3(CH2)3 NaOH, H2O CH3 O CH3(CH2)3 4d – O CH3CCH2CO2CH3 e five CH2 1) NaH CH2 2) RLi O– O– CCH COCH3 + (CH3)2C O O– CCH COCH3 CHCH2Br CH3 CH3 O 2 eq. LDA DMPU O O 1) C2H5Br CH3(CH2)2CCH2CO2CH3 2) H3O+ eighty four% O 1) CH3 6f fifty four –74% CH3 – O SPh – SPh 2) (CH3)2C CH3 O CH2CH2Br CHCH2CH2CCH2CO2CH3 eighty five% CH3 O CH3 CH3 CH3 O Al O 37% O O a. T. M. Harris, S. Boatman, and C. R. Hauser, J. Am. Chem. Soc. , eighty five, 3273 (1963); S. Boatman, T. M. Harris, and C. R. Hauser, J. Am. Chem. Soc. , 87, eighty two (1965); okay. G. Hampton, T. M. Harris, and C. R. Hauser, J. Org. Chem. , 28, 1946 (1963). b. okay. G. Hampton, T. M. Harris, and C. R. Hauser, Org. Synth. , forty seven, ninety two (1967). c. S. Boatman, T. M. Harris, and C. R. Hauser, Org. Synth. , forty eight, forty (1968). d. S. N Huckin and L. Weiler, J. Am. Chem. Soc. , 96,1082 (1974). e. F. W. Sum and L. Weiler, J. Am. Chem. Soc. , a hundred and one, 4401 (1979). f. M. A. Avery, W. okay. M. Chong, and C. Jennings-White, J. Am. Chem. Soc. , 114, 974 (1992). formation of the trans ring junction will be extra strained as a result of the necessity to span the space to the other face of the enolate procedure. O– (CH2)4OSO2Ar 7 ArSO3 CH3 CH3 H H eight O– H O O– O3SAr F G 38 bankruptcy 1 Alkylation of Enolates and different Carbon Nucleophiles Geometric elements within the TS also are chargeable for variations with regards to cyclization of enolates nine and 10. eighty four H (CH3)3C H O– H CH2 nine CH2CH2Br –O H H O (CH3)3C four eq HMPA in ether, 25oC H four eq HMPA in ether, 25oC CH2 (CH3)3C THF reflux or H (CH3)3C 10 CH2CH2Br eighty one ± five% O this cyclization is slower than for the cis isomer and there's a few aggressive epimerization. H a couple of examples of excellent stereoselectivity in accordance with substituent regulate of reactant conformation were pointed out. for instance, eleven provides greater than ninety six% stereoselectivity for the isomer within which the methyl and 2-propenyl teams are cis. eighty five S S eleven OTs CH3 CO2C2H5 THF H CH3 CH3 S KHDMS S –78°C CO2C2H5 H CH3 related cis stereoselectivity used to be saw in formation of 4- and 5-membered jewelry. 86 The starting place of this stereoselectivity was once probed systematically via a research during which a methyl substituent used to be positioned on the C(3), C(4), C(5), and C(6) positions of ethyl 7-bromoheptanoate.