Single route to chiral syn- and anti-2-amino-1,2-diphenylethanols via a new stereodivergent opening of trans-1,2-diphenyloxirane.
Oxiranyl ring opening of trans-stilbene oxide gave rise to anti- or syn-2-bromo-1,2-diphenylethanols, using either MgBr(2).Et(2)O or MgBr(2).Et(2)O, NaBr, and KBr with Amberlyst 15, respectively. Starting from optically pure (R,R)-trans-stilbene oxide, (1R,2R)- and (1R,2S)-2-amino-1,2-diphenylethanols were obtained in high yield and ee.
Lupattelli
Paolo
P
Dipartimento di Chimica, Università degli Studi della Basilicata, via Nazario Sauro 85, 85100 Potenza, Italy. lupattelli@unibas.it
Bonini
Carlo
C
Caruso
Leonilde
L
Gambacorta
Augusto
A