An efficient route to tetrahydronaphthols via addition of ortho-lithiated stilbene oxides to alpha,beta-unsaturated fischer carbene Complexes.
[reaction: see text] A stereoselective/stereospecific synthesis of polysubstituted tetrahydronaphthols based on the Michael addition of ortho-lithiated stilbene oxides to alpha,beta-unsaturated Fischer carbene complexes followed by an unusual cyclization of the corresponding intermediate in a 6-endo-tet mode is described.
Capriati
Vito
V
Dipartimento Farmaco-Chimico, University of Bari, Italy.
Florio
Saverio
S
Luisi
Renzo
R
Perna
Filippo Maria
FM
Salomone
Antonio
A
Gasparrini
Francesco
F
D003500:Cyclization; D006838:Hydrocarbons / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D046911:Macromolecular Substances / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*
D006838:Hydrocarbons; D046911:Macromolecular Substances; D009284:Naphthols; D013267:Stilbenes; C030011:carbene; D008094:Lithium; C025906:stilbene oxide; D008697:Methane