10.1002/ejoc.201900588
European Journal of Organic Chemistry
COMMUNICATION
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and 12e, entries 1,2 and 5). In the case of 3-fluoro derivative
12d the corresponding product 13d was obtained as promising
80/20 syn/anti mixture (entry 4). Only in the case of 4-
methoxyphenylboronic acid 12c the regio- and stereoselectivity
of the reaction dropped dramatically, affording an equimolar
mixture of the four possible ring opening products. Better results
were achieved using 3-methoxyphenylboronic acid 12e and
almost equimolar mixture of syn/anti 13e and the other
regioisomer (probably syn) was obtained. This last result
appeared quite unexpected suggesting for the first time an effect
of the nucleophilic character of the incoming reagent on the
selectivity of the reaction. Dioxofunctionalized epoxides 1e and
1f were also tested with 4-bromophenylboronic acid 12a
affording the corresponding syn arylalcohols 13g and 13h with
good yield and high selectivity. Thus the method appears of
wide scope in the preparation of polyfunctionalised trans 3-aryl-
2-phenyl-2,3-dihydrobenzofurans.
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Conclusion
A series of ortho oxo substituted trans diaryloxiranes was regio-
and stereoselectively opened by PhB(OH)2/Et2Zn system,
allowing stereoselective access to trans 2,3-diphenyl-2,3-
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Financial support has been provided by MIUR (Italian Ministry of
University) PON Ricerca
e Innovazione 2014–2020 - Area
SALUTE - ARS01 01081, “Prodotti INnovativi ad alto contenuto
biotecnologico per il settore BIOMEDicale” (INBIOMED) and
University of Basilicata. We also thank MIUR for PhD grant to TL
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