Michael addition initiated carbocyclization sequences with nitroolefins for the stereoselective synthesis of functionalized heterocyclic and carbocyclic systems.
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.
Dumez
Estelle
E
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille iSm2 CNRS UMR 6263, Centre Saint Jérôme service 531-13397 Marseille Cedex 20, France.
Durand
Anne-Catherine
AC
Guillaume
Martial
M
Roger
Pierre-Yves
PY
Faure
Robert
R
Pons
Jean-Marc
JM
Herbette
Gaëtan
G
Dulcère
Jean-Pierre
JP
Bonne
Damien
D
Rodriguez
Jean
J
D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D003517:Cyclopentanes; D003521:Cyclopropanes; D005663:Furans; D006571:Heterocyclic Compounds