M. Carmen Murcia

Regioselective domino metathesis of 7-oxanorbornene derivatives as a new stereoselective entry into 2,6-dioxabicyclo[4.3.0]nonenes

Abstract Domino metathesis of allyl- and propargyl-(2-endo-7-oxanorborn-5-enyl) ethers with allyl acetate in the presence of Grubbs’ ruthenium catalyst affords stereoselectively substituted cis-fused bicyclic ethers (2,6-dioxabicyclo[4.3.0]non-8-enes).

The Staudinger reaction of imines derived from 7-oxanorbornenone: formation of spiranic oxazinone versus β-lactam rings

The Staudinger reaction of imines derived from 7-oxanorbornenone with 2-alkoxyacetyl chlorides afforded spiro-β-lactams albeit with an unexpected stereochemistry. This was not the case with arylacetic acid chlorides, which gave rise to spiranic oxazinone rings as well as the expected β-lactams.

On the reactivity of (7-oxabicyclo[2.2.1]hept-5-en-2-ylidene)amines. Different reaction paths leading to the same final products

The reaction of amines, N-substituted by a 7-oxabicyclo[2.2.1]hept-5-en-2-ylidene moiety, either with PhSCl or mCPBA (meta-chloroperbenzoic acid) unexpectedly afforded the same type of furan derivatives by two different reaction paths. The results confirm the intervention of a homoconjugative, electron-releasing effect of the oxabicycloalkenylideneamine moieties, as predicted theoretically.