Organic Syntheses by Boeckman R.K., Coffen D.L., Overman L.E. (eds.)

By Boeckman R.K., Coffen D.L., Overman L.E. (eds.)

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Sample text

This might be considered to run counter to a number of other analyses of reactivity and selectivitv. E I , . , O R, ( ) 9. M. T. Reetz, Accounts of Chemical Research 1993,26,462 10. D. J. Cram, K. R. Kopecky, Journal of the American Chemical Society 1959, 11. a. b. c. d. a,2748 W. C. Still, J. H. McDonald, TetrahedronLetters, 1984, 1031 M. T. Reetz, Angewandte Chemie, International Edition in English, 1984,23, 556 G. E. Keck, D. E. Abbott, Tetrahedron Letters 1984,25, 1883 S. V. Frye, E. L. Eliel, Journal ofthe American Chemical Society 1988,110,484 12.

Methew, Journal ofthe Chemical Society 1959, 112 24 Name Reaction Chelation Controp Neighboring heteroatoms can provide a site for complexing. , 0 rT1, ~1 A1 2c R Het = heteroatom h4 M =metal Product stereochemistries can be greatly influenced by these chelation control effects. ” These concepts are seen on the energy diagram below. It should be noted that an interesting conclusion from this analysis is that increased selectivity is associated with increased reactivity. This might be considered to run counter to a number of other analyses of reactivity and selectivitv.

Houlihan, Organic Reactions 16 (full volume); T. Mukaiyama, Organic Reactions, 28, 3; C. J. Cowden, I. Patterson, Organic Reactions 51, 1 . /CHO H20 Me 86% M. Hausserrnann, Helvetica Chimica Acta 1951,34, 1482 (Reported in A. T. Nielsen, W. J Houlihan, Organic Reactions 16, page 8). P. M. , R. K. Singh, Journal of Organic Chemistvy 1974,39,2316 NaOH i-PrO S MeJ 50% i-Pr Me E. J. Corey, S. Nozoe, Journal ofthe American Chemical Society 1965,Sl, 5728 0 s M e A N K s I Me TiCh, TMEDA, PhCHO 3. Me Me 62% 7;'u97 Me Me Me Me M.

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