Synthetic methods in organic and supramolecular chemistry by Colleen Nicola Scott

By Colleen Nicola Scott

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16. ; Dick, K. Tetrahedron Lett. 1982, 23, 3167. ; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420. ; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5410. 17. ; Koga, K. Tetrahedron Lett. 1984, 25, 973. 18. ; Wilcox, C. J. Am. Chem. Soc. 1988, 110, 6204. 19. Tröger, J. Prakt. Chem. 1887, 36, 225. 20. Goecke, G. Elektrochem. 1903, 9, 470. 21. ; Wieland, P. Helv. Chim. Acta. 1944, 27, 1127. 22. Wilcox, C. Tetrahedron Lett. 1988, 26, 5749. 23. ; Wilcox, C. Tetrahedron Lett. 1986, 27, 5563. (b) Sucholeiki, I.

Chem. Int. Ed. Engl. 1988, 27, 1009. (f) Cram, D. J. Incl. Phenom. 1988, 6. 3. (a) Cram, D. J. From Design to Discovery; American Chemical Society: Washington, DC, 1990, p 91. (b) Cram, D. ; Trueblood, K. N. Topp. Cur. Chem. 1981, 98, 43. 4. (a) Ben-Naim, A. Hydrophobic Interactions; Plenum Press: New York, 1980. (b) Tanfrod, C. ; Wiley: New York, 1980. 5. ; Trueblood, K. ; Springer-Verley Berlin Heiddberg New York Tokyo, 1985. 6. ; Gratheer, H. Liebigs. Ann. Chem. 1942, 550, 67. 7. Cram, D. ; Steiberg, H.

Conditions Applied to the Buchwald-Hartwig Reaction. Entry Aryl Amine Condition Ligand % yield of Compound Product 1 A BINAP 70 A BINAP 0 3 B BINAP 0 4 C 1 0 C 1 60 C 2 96 C 2 0 8 D 2 0 9 E 2 60 O N H OTf 2 H N 5 H N Br 6 7 O O O H N O Br 10 Host 17 (d/l) E 2 nmr product 11 Host 17 (meso) E 2 21 Conditions: A: Cs2CO3, Pd(OAc)2, Tol, 80 ºC B: NatOBu, Pd(OAc)2, Tol, 80 ºC C: NatOBu, Pd2(dba)3, Tol, 80 ºC D: NatOBu, Pd2(dba)3, THF, 80 ºC E: K3PO4, Pd2(dba)3, Tol, 80 ºC PPh2 t P( Bu)2 P(cy)2 PPh2 R,S-BINAP 28 Ligand 1 Ligand 2 O O O O O H2SO4, Br2, Ag2SO4 HO HO OH OH NaHCO3, HMPA isopropyl iodide 90 % O O O 87 % Br Br 37 38 Scheme 14.

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