171107-79-2Relevant academic research and scientific papers
Synthesis of bridged azabicyclic compounds using raducal translocation reactions of 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidines
Sato, Tatsunori,Kugo, Yasuhiro,Nakaumi, Erina,Ishibashi, Hiroyuki,ikeda, Masazumi
, p. 1801 - 1810 (2007/10/02)
A new synthesis of the 7-azabicycloheptane and 8-azabicyclooctane systems is described in which α-acylamino radicals generated from 1-(o-bromobenzoyl-2-(prop-2-enyl)pyrrolidines by a Bu3SnH-mediated radical translocation reaction are cyclised.Treatment of methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine-2-carboxylate 3a with Bu3SnH in the presence of a catalytic amount of azoisobutyronitrile in boiling toluene gave the 7-azabicycloheptane 4a (a 5-exo cyclisation product) and the 8-azabicyclooctane 5a (a 6-endo product) (30percent), together with the reduction product 6a (12percent).The geriochemistry (5-exo/6-endo) of this cyclisation could be controlled by the introduction of a substituent on the prop-2-enyl group.The substituent(s) at the 2- and/or 4-position(s) of the pyrrolidine ring were found to play an important role in this cyclisation.
