Organic Synthesis Highlights 5Vset by Waldmann

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Mukhopadhyay, and E. Thomas, Helv. Chim. Acta. 65, 1101 (1982). D. Seebach and P. Knochel, Helv. Chim. Acta 67, 261 (1984). M. Eberle, M . Egli, and D. Seebach, Helv. Chim. Acta 71, 1 (1988). [9] M. E. Kuehne and L. Foley, J. Org. Chem. 30, 4280 (1965); A. Risaliti, M. Forchiassin. and E. Valentin, Tetrahedron Lett. 1966, 6331. [lo] D. Seebach, A. K. Beck, J. Golihski, J. N . Hay, and T. Laube, Helv. Chim. Acta 68, 162 (1985); for a directed synthesis of the epimer of (21), see: D. Seebach and M .

Cited; b) NaBH4: F. Rolla, J. Org. Chem. 47,4327 (1982); c) catalytic hydrogenations see ref. [23]. 1201 M. Regitz, Synthesis 1972, 351. [21] a) S. J. Weininger, S. Kohen, S. Mataka, G. -P. Anselme, J. Org. Chem. 39,1591 (1975) and ref. cited; b) Sulfonyl azides: P. A. S. Smith, C. D. Rowe, and L. B. Brunner, J. Org. Chem. 34, 3430 (1969). [22] J. N. Reed and V. Snieckus, Tetrahedron Lett. 24, 3795 (1983). 53 [23] G. H. Hakimelahi and G. Just, Synth. Commun. 10, 429 (1980). [24] N . -C. Joo, J.

The work of Regitz [20] initially revealed that tosyl azide could act as a diazo transfer reagent, and only later were its properties as an azido transfer reagent investigated [21]. The reagent has found broader application in connection with the ortho-selective metalation of aromatic benzamides. The three step process metalation, conversion to an azide, and phase-transfer catalyzed borohydride reduction gives amines in quite Electrophilic Aminations satisfactory yields (43 - 71%, nine examples).

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