The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalities through chelation processes assisted by metal ions was verified in a conformationally semirigid cyclic oxirane system in which the polar functionality is both directly inserted into the cyclic system and present on the cyclic system itself. Diastereoisomeric cis 4 and trans epoxide 5, derived from 2-(benzyloxy)-3,6-dihydro-2H-pyran, were prepared and some of their opening reactions (azidolysis, aminolysis, Cl- addition, and LiAlH4 reduction) were studied. The regioselectivity observed is largely dependent for both 4 and 5 on the opening (standard or metal-assisted) reaction conditions, and a regioalternating process is almost obtained.
|Autori interni:||CROTTI, PAOLO|
|Autori:||CHINI M; CROTTI P; GARDELLI C; MACCHIA F|
|Titolo:||REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .7. SYNTHESIS AND RING-OPENING REACTIONS OF CIS-OXIDE AND TRANS-OXIDE DERIVED FROM 2-(BENZYLOXY)-3,6-DIHYDRO-2H-PYRAN|
|Anno del prodotto:||1994|
|Digital Object Identifier (DOI):||10.1021/jo00094a025|
|Appare nelle tipologie:||1.1 Articolo in rivista|