The Journal of organic chemistry

A Convenient New Route to Piperidines, Pyrrolizidines, Indolizidines, and Quinolizidines by Cyclization of Acetylenic Sulfones with β-and γ-Chloroamines. …

TG Back, K Nakajima

Index: Back, Thomas G.; Nakajima, Katsumasa Journal of Organic Chemistry, 2000 , vol. 65, # 15 p. 4543 - 4552

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Citation Number: 100

Abstract

The methyl esters of (l)-phenylalanine and (l)-methionine underwent conjugate additions via their free amino groups to 1-(p-toluenesulfonyl) hexyne, followed by intramolecular acylation of the corresponding enamide anions and tautomerization to afford 2-benzyl-5-n-butyl-3- hydroxy-4-(p-toluenesulfonyl) pyrrole and 5-n-butyl-3-hydroxy-2-(2-methylthioethyl)-4-(p- toluenesulfonyl) pyrrole, respectively. The conjugate additions of a series of acyclic and ...