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Organis syntheis. Strategy and control by Wyatt P., Warren S.

By Wyatt P., Warren S.

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1972, 892; J. L. Herrmann and R. H. Schlessinger, J. Chem. , Chem. , 1973, 711. 11. Disconnection Approach, page 160. 12. M. W. Rathke, J. Am. Chem. , 1970, 92, 3222; M. W. Rathke and D. F. Sullivan, J. Am. Chem. , 1973, 95, 3050; M. W. Rathke, Organic Syntheses, 1973, 53, 66. 13. Disconnection Approach, page 149, 158. 14. P. Grieco, J. Chem. , Chem. , 1972, 1317. 15. A. P. Krapcho and E. G. E. Jahngen, J. Org. , 1974, 39, 1322. 16. P. L. Creger, J. Am. Chem. , 1970, 92, 1397; P. E. Pfeiffer, L.

J. Bestmann, J. Süss and O. Vostrowsky, Liebig’s Annalen, 1981, 2117. 7. D. Diederich, Houben-Weyl, 1973, 7/2a, page 958. 8. E. J. Corey, M. Ohno, R. B. Mitra, and P. A. Venkatacherry, J. Am. Chem. , 1964, 88, 478. 9. R. J. Cregge, J. L. Herrmann, C. S. Lee, J. E. Richman and R. H. , 1973, 2425. 10. G. Posner and G. L. Loomis, J. Chem. , Chem. , 1972, 892; J. L. Herrmann and R. H. Schlessinger, J. Chem. , Chem. , 1973, 711. 11. Disconnection Approach, page 160. 12. M. W. Rathke, J. Am. Chem. , 1970, 92, 3222; M.

The ketone 15 forms mostly the less substituted lithium enolate which condenses 29 with butanal to give aldol 31 in reasonable yield. Elimination is usually carried out in acid solution. O O Li O O OLi LDA 29 15 O 30 O OH work-up TsOH enone 32 aldol 31 Contrast with equilibrium methods Traditional equilibration methods [mix 15, PrCHO and NaOH] would give the enal 33 from self-condensation of butanal. The aldehyde would ignore the less enolisable and less electrophilic ketone. 13 The titanium atom bonds to both oxygen atoms (of the enolate and the aldehyde) 36.

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