Diastereoselective Cyclisation of  N ‐Alkenylideneamines into 3,4‐Dihydro‐2 H ‐pyrrol‐1‐ium Halides | Zendy

Schley Daniela | Zendy; Liebscher Jürgen | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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)

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research