Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.
A new torquoselective ring-closure of chiral amide-substituted 1,3,5-hexatrienes and its application in tandem with [4 + 2] cycloaddition are described. The trienes were derived via either a 1,3-H or 1,3-H-1,7-H shift of alpha-substituted allenamides, and the entire sequence through the [4 + 2] cycloaddition could be in tandem from allenamides.
Hayashi
Ryuji
R
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
Feltenberger
John B
JB
Hsung
Richard P
RP
D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D011090:Polyenes; C512191:1,3,5-hexatriene