Highly diastereoselective three-component vinylogous Mannich reaction between isoquinolines, acyl/sulfonyl chlorides, and silyloxyfurans.
Reaction of an isoquinoline, a silyloxyfuran, and an acyl or sulfonyl chloride provides easy access to a wide variety of isoquinolinobutyrolactones with excellent yields and diastereoselectivites (R*,R* isomer), even in the case of formation of quaternary centers (i.e., R(3) or R(4) = Me). Moreover, the use of a chiral auxiliary allowed formation of a single stereoisomer in 96% yield. This represents the first examples of asymmetric vinylogous Mannich reactions on isoquinolinium salts.
Hermange
Philippe
P
Institut de Chimie des Substances Naturelles - CNRS UPR 2301, Gif-sur-Yvette, France.
Tran Huu Dau
Marie Elise
ME
Retailleau
Pascal
P
Dodd
Robert H
RH
D002384:Catalysis; D007536:Isomerism; D007546:Isoquinolines / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*
D007546:Isoquinolines; D013441:Sulfinic Acids; C044255:sulfonyl chloride