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Applications I. Main Group Compounds in Organic Synthesis by Knochel P.

By Knochel P.

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Schlosser, M. Tetrahedron 1990, 46, 2411. ; Mioskowski, C. Angew. , Int. Ed. 2002, 41, 340–343. ; Desmurs, J. ; Jost, S. (Rhodia Chimie). WO 0064905, 2000. ; Desmurs, J. ; Gissot, A. (Rhodia Chimie). WO 9959941, 1999. Feringa, B. ; Brandsma, L. Synthesis 1988, 316. ; Schlosser, M. Tetrahedron 1993, 49, 10271. ; George, A. V. ; de Jong, R. L. ; Brandsma, L. J. Chem. , Chem. Commun. 1984, 257. ; Brandsma, L. J. Org. Chem. 1984, 49, 3857. ; Que´guiner, G. Tetrahedron 2001, 57, 4059. ; Que´guiner, G.

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190 Acyl chlorides react with Grignard reagents in the presence of 5% Fe(acac)3 already at À78  C. At this temperature undesired side-reactions like the attack on the resulting ketone are completely suppressed. 191 Alternatively, acyl halides first react with tri-n-butylphosphine to form acylphosphonium salts. 195,196 Thus, a protected pseudoephedrine glycinamide is first diastereoselectively alkylated in the presence of a base. 5–20 h 70–93% NHBoc R1 R >95% ee Magnesium Symmetrical -diones,198,199 carboxylates,200 tertiary amides,201 and thioamides202,203 are obtained from Grignard reagents in one-pot syntheses.

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