Premium
N ‐Alkoxyacrylamides in Domino Reactions: Catalytic and Stereoselective Access to δ‐Lactams
Author(s) -
Champetter Philippe,
CastilloAguilera Omar,
Taillier Catherine,
Brière JeanFrançois,
Dalla Vincent,
Oudeyer Sylvain,
Comesse Sébastien
Publication year - 2019
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.201901528
Subject(s) - domino , stereoselectivity , reactivity (psychology) , catalysis , michael reaction , intramolecular force , chemistry , alkoxy group , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , alkyl , alternative medicine , pathology
The first domino aza‐Michael/intramolecular‐Michael reaction employing acrylamides as key ambivalent partners for the synthesis of δ‐lactams is presented. It has been shown that the desired reactivity is contingent to the presence of an N ‐alkoxy group within the acrylamides. Thus, in a base‐catalyzed process that operates under mild conditions, N ‐alkoxyacrylamides are readily converted into polysubstituted δ‐lactams in good yields with good to excellent stereocontrol.