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  • An efficient route to tetrahydronaphthols via addition of ortho-lithiated stilbene oxides to alpha,beta-unsaturated fischer carbene Complexes.

An efficient route to tetrahydronaphthols via addition of ortho-lithiated stilbene oxides to alpha,beta-unsaturated fischer carbene Complexes.

Organic letters (2005-10-21)
Vito Capriati, Saverio Florio, Renzo Luisi, Filippo Maria Perna, Antonio Salomone, Francesco Gasparrini
ABSTRACT

[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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
cis-Stilbene oxide, 97%
Sigma-Aldrich
trans-Stilbene oxide, 98%