Synthesis of 20-deethylsilicine from a second-generation 2-cyano-. DELTA. 3-piperidine synthon

DS Grierson, JL Bettiol, I Buck, HP Husson…

Index: Grierson, David S.; Bettiol, Jean-Luc; Buck, Ildiko; Husson, Henri-Philippe; Rubiralta, Mario; Diez, Anna Journal of Organic Chemistry, 1992 , vol. 57, # 24 p. 6414 - 6421

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Citation Number: 17

Abstract

The Zn2+ ion mediated reaction of the 2-cyano-A33-piperidine Sa (X= SO&H5) with the silyl enol ether of Na-methyl-2-acetylindole (24) led to formation of compounds 29a, b (70%) resulting from introduction of the acetylindole moiety at the exocyclic (C-7) carbon center and migration of the phenylsulfonyl group from C-7 to C-4. In contrast, reaction of 2-cyano- A3-piperidine 9b (X= CN) with 24 gave the desired C-4 acetylindolesubstituted producta ...