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Endocyclic Enamides Derived from Aza‐Diketopiperazines as Olefin Partners in Povarov Reaction: An Access to Tetracyclic N‐Heterocycles
Author(s) -
Maujean Timothé,
Chataigner Isabelle,
Girard Nicolas,
Gulea Mihaela,
Bonnet Dominique
Publication year - 2020
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.202001339
Subject(s) - chemistry , diketopiperazines , cycloaddition , aldehyde , olefin fiber , catalysis , bicyclic molecule , lewis acids and bases , stereochemistry , organic chemistry , combinatorial chemistry
Original endocyclic enamides based on a bicyclic aza‐diketopiperazine (aza‐DKP) structure have been used as dienophile partners in the Povarov reaction. The reported method represents a successful strategy for the structural diversification of the aza‐DKP scaffold, giving access to a new family of fused tetracyclic N ‐heterocycles, which contain at least four nitrogen atoms in the heterocyclic structure. Depending on the nature of the aldehyde partner, the cycloadditions have been performed either as a two‐component or a three‐component Povarov reaction (2CPR or 3CPR), in the presence of BF 3 as a Lewis acid catalyst. With aliphatic aldehydes the reaction proceeds with high diastereoselectivities in favor of the cis compounds. Some mechanistic aspects of this cycloaddition have been examined computationally.