By Manfred T. Reetz (auth.)
Content material: Organotitanium reagents in natural synthesis: an easy capability to regulate reactivity and selectivity of carbanions / M.T. Reetz -- Lithium halocarbenoids--carbanions of excessive man made versatility / H.J. Siegel -- Pyridinophanes, pyridinocrowns, and pyridinocryptands / V.K. Majestic, G.R. Newkome -- New views in polymer-supported peptide synthesis / V.N R. Pillai, M. Mutter
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Extra info for Synthetic and Structural Problems
Since the diastereoselectivities in these reactions are seldom above 90 ~, the advantage of not having to prepare prochirally pure enolates is not that apparent. The situation in cyclic ketones is a little different, since the corresponding lithium, magnesium and boron E enolates react threo-selectively. , Equation 66 25) OLi OTi[OCHMe2} 3 193 0 19,~ OH C~ ~ 195 I96 a R = CsH s 86 : 1/, b R = CH(CH3) 2 96 : /, (66) Variation of the ligands at titanium can lead to improvements. For example, enolates 197a-b react with benzaldehyde to afford 92:8 and 97:3 mixtures of 195a and 196a, respectively 25k Enolates 199-202, derived from ketones, lactones and lactams, add erythro-selectively to benzaldehyde to yield the corresponding aldols (erythro: threo as 85:15, 91:9, 92:8, 58:42 and 88:12, respectively) 2s,77).
Angew. Chem. 92, 933 (1980); Angew. , Int. Ed. Engl. 19, 901 (1980) 75. Reetz, M. T. , Frankfurt 1980 76. : Helv. Chim. Acta 63, 2451 (1980) 77. Reetz, M. T. et al. : unpublished results, Univ. Marburg 1980-82 78. Weidmann, B. : Helv. Chim. Acta 64, 357 (1981) 79. Reetz, M. , Maus, S. : in prepa~ration 80. , Maycock, C. : Helv. Claim. Acta 64, 1552 (1981) 8 I. TiC14and Ti(OR)4 are cheap raw materials used in large quantities in industry. Zirconium analogs cost about 3-4 times as much 82. Reetz, M.
46, 4292 (1981) and lit. cited therein; c) Rieke, R. D. : Acc. Chem. Res. 10, 301 (1977) t2. : Angew. Chem. 89, 858 (1977); Angew. , Int. Ed. Engl. 16, 817 (1977) 13. Reetz, M. : Angew. Chem. 94, 97 (1982); Angew. , Int. Ed. Engl. 21, 96 (1982) 14. Chan, T. : Synthesis 1979, 761 15. See for example: Chem. Abstr. 61: 4223f (1964); 67: 73173b (1967); 74: 100452v (1971) 16. Seebach, D. et al. : Synthesis 1982, 138 17. ,,Tiians/iureester", Information Pamphlet, Dynamit Nobel AG, Troisdorf, W-Germany 18.
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