REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OFCHELATING PROCESSES .7. SYNTHESIS AND RING-OPENING REACTIONS OF CIS-OXIDE AND TRANS-OXIDE DERIVED FROM 2-(BENZYLOXY)-3,6-DIHYDRO-2H-PYRAN
M. Chini et al., REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OFCHELATING PROCESSES .7. SYNTHESIS AND RING-OPENING REACTIONS OF CIS-OXIDE AND TRANS-OXIDE DERIVED FROM 2-(BENZYLOXY)-3,6-DIHYDRO-2H-PYRAN, Journal of organic chemistry, 59(15), 1994, pp. 4131-4137
The regiochemical outcome of the ring opening of 1,2-epoxides bearing
polar remote functionalities through chelation processes assisted by m
etal 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. Diastereoi
someric cis 4 and trans epoxide 5, derived from 2-(benzyloxy)-3,6-dihy
dro-2H-pyran, were prepared and some of their opening reactions (azido
lysis, aminolysis, Cl- addition, and LiAlH4 reduction) were studied. T
he regioselectivity observed is largely dependent for both 4 and 5 on
the opening (standard or metal-assisted) reaction conditions, and a re
gioalternating process is almost obtained.