Synthesis of 2??Phenyl??and 2, 2??Diarylpyrrolidines through Stevens Rearrangement Performed on Azetidinium Ions

B Drouillat, E d'Aboville, F Bourdreux…

Index: Drouillat, Bruno; D'Aboville, Edouard; Bourdreux, Flavien; Couty, Francois European Journal of Organic Chemistry, 2014 , vol. 2014, # 5 p. 1103 - 1109

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Citation Number: 4

Abstract

Abstract A set of azetidinium ions substituted at the nitrogen atom either by a benzyl group or a benzhydryl group were synthesized to delineate the scope of their ring expansion into 2- phenyl-or 2, 2-diaryl-pyrrolidines through a Stevens rearrangement. Whereas the regioselectivity of the rearrangement is very high, the diastereoselectivity is low when 2, 3- disubstituted pyrrolidines are produced, except in one case. The major undesirable side- ...