571167-47-0Relevant articles and documents
Copper-catalysed addition of organometallic reagents to vinyl diepoxides - A novel route to oxa-bridged systems and to substituted allylic alcohols
Bertozzi, Fabio,Crotti, Paolo,Del Moro, Federica,Di Bussolo, Valeria,Macchia, Franco,Pineschi, Mauro
, p. 1264 - 1270 (2003)
The copper-catalysed addition of organometallic reagents (Grignard and dialkylzinc) to new vinyl diepoxides was examined. Cyclic vinyl diepoxides undergo clean SN2′ reactions to afford oxa-bridged systems of various sizes after a domino intramolecular O-alkylation reaction. Acyclic vinyl diepoxides are alkylated in good yields and with good regioselectivities, and a new catalytic enantioselective desymmetrization reaction to afford an enantioenriched allylic epoxy alcohol by the use of catalytic amounts of a copper phosphorarnidite complex was demonstrated. Remarkable differences in terms of reactivity and selectivity are found when different organocopper reagents, generated in situ, are employed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.