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- Title
Intramolecular Bromoamination of Conjugated N-Tosylaminodienes Using N-Bromosuccinimide. Synthesis of Bromoallyl-Substituted N-Heterocycles and Their Applications as Building Blocks.
- Authors
Márquez‐Segovia, Isabel; Baeza, Alejandro; Otero, Antonio; Nájera, Carmen
- Abstract
The bromonium-promoted cyclization of conjugated aminodienes is described. The reaction proceeds smoothly in the presence of N-bromosuccinimide as halonium promoter, and using N-tosyl-protected aminodienes as substrates, to give the corresponding halocyclization products in high yields and with high diastereoselectivities. It can be envisaged that the formation of these products is the result of an SN2′-type ring-opening of a terminal bromonium intermediate in a 5- exo- trig or 6- exo- trig cyclization mode. The presence of an allyl bromide moiety in the haloamination products makes these molecules highly attractive from a synthetic point of view, as it opens the way for further transformations. Thus, allylic substitution reactions with different nucleophiles (acetate, azide, cyanide, and malonate), palladium-catalysed Suzuki coupling, and silver-mediated bromine displacement reactions were carried out successfully.
- Subjects
SPECTRUM analysis; BROMINE; HETEROCYCLIC compounds; BLOCKS (Building materials); BROMOSUCCINIMIDE; ALLYL alcohol synthesis; PALLADIUM; CYANIDES synthesis; SUZUKI reaction
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 22, p4962
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300444