Monodeazacinchona Alkaloid Derivatives: Synthesis and Preliminary Applications as Phase-Transfer Catalysts

Abstract

Four analogues of cinchona alkaloids (5−8) lacking the quinoline nitrogen atom have been prepared. Quaternization afforded the phase-transfer catalysts 10a, 10b, 11a, and 12d. Other optically active catalyst salts were prepared from the cinchona alkaloids themselves (compounds 13, 14, 15). The performances of these PT catalysts and of some others were compared in three test reactions. The deazacinchona derivatives exhibited selectivities similar to or sometimes even better than those of the natural product-derived compounds. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)