Selective synthesis of cis-2-vinyl-3-alkylaziridines and 3-pyrrolines from common intermediates (Z)-4-N-arylsulfonylaminoalk-2-en-1-ols

…, H Ohno, Y Takemoto, E Osawa, Y Yamaoka…

Index: Ishii, Kiyonori; Ohno, Hiroaki; Takemoto, Yoshiji; Osawa, Eriko; Yamaoka, Yumiko; Fujii, Nobutaka; Ibuka, Toshiro Journal of the Chemical Society - Perkin Transactions 1, 1999 ,  # 15  p. 2155 - 2163

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Abstract

A simple method for the synthesis of both cis-2-vinylaziridines and 3-pyrrolines from common intermediate (Z)-4-(N-arylsulfonyl) amino-4-alkylbut-2-en-1-ols, is described. Palladium (0)-catalyzed reactions of methyl carbonates of the N-protected (Z)-4-amino-4- alkylbut-2-en-1-ols yield predominantly cis-3-alkyl-2-vinylaziridines. Alternatively, upon exposure to sodium hydride, methanesulfonates derived from N-protected (Z)-4-amino-4- ...