Addition of lithiated methoxyallene to aziridines–a novel access to enantiopure piperidine and β-amino acid derivatives

V Prisyazhnyuk, M Jachan, I Brüdgam…

Index: Prisyazhnyuk, Vladimir; Jachan, Matthias; Bruedgam, Irene; Zimmer, Reinhold; Reissig, Hans-Ulrich Collection of Czechoslovak Chemical Communications, 2009 , vol. 74, # 7-8 p. 1069 - 1080

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Citation Number: 6

Abstract

Abstract Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or β-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone ...

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