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Diastereoselective Cyclisation of N ‐Alkenylideneamines into 3,4‐Dihydro‐2 H ‐pyrrol‐1‐ium Halides
Author(s) -
Schley Daniela,
Liebscher Jürgen
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601081
Subject(s) - chemistry , diastereomer , asymmetric induction , substituent , alkyl , reagent , halide , chirality (physics) , enantioselective synthesis , substrate (aquarium) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , chiral symmetry , nambu–jona lasinio model , physics , oceanography , quantum mechanics , quark , geology
A number of new chiral 2‐(α‐bromoalkyl)pyrrolinium salts and 2‐(α‐selenoalkyl)pyrrolidines were synthesized by the halocyclisation and selenocyclisation, respectively, of N ‐(alkenylidene)alkylamines and subsequent reduction. These cyclisations were implemented in a diastereomeric fashion for the first time. Substrate control (starting imines possessing chirality in the N ‐alkyl or the N ‐alkenyl substituent) and reagent control (chiral organoselenenyl bromides) wereapplied. Asymmetric induction by stereocentres of the alkenylidene or double asymmetric induction by chiral selenenyl bromides on unsaturated imines with a chiral N ‐alkyl group resulted in diatereoselectivities up to 84:16. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)