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Michael Addition Initiated Carbocyclization Sequences with Nitroolefins for the Stereoselective Synthesis of Functionalized Heterocyclic and Carbocyclic Systems
Author(s) -
Dumez Estelle,
Durand AnneCatherine,
Guillaume Martial,
Roger PierreYves,
Faure Robert,
Pons JeanMarc,
Herbette Gaëtan,
Dulcère JeanPierre,
Bonne Damien,
Rodriguez Jean
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901433
Subject(s) - stereocenter , stereoselectivity , cyclopentanes , chemistry , michael reaction , nucleophile , organic chemistry , malonate , oxonium ion , cyclopentane , combinatorial chemistry , stereochemistry , enantioselective synthesis , catalysis , ion
The synthesis of various heterocycles and carbocycles (tetrahydrofurans, pyrrolidines, cyclopentanes) has been achieved by using new and efficient ionic addition/cyclization sequences. Nitroolefins play an important role in the Michael addition induced ring‐closing reactions (MIRC) reported in the present article, with various substituted alcohols, amines, Grignard reactants, or malonate derivatives acting as the nucleophile partner. The optimized cascade reactions were high yielding in most cases and highly stereoselective, creating up to three stereogenic centers starting from achiral substrates.