Single Route to Chiral syn- and anti-2-Amino-1,2-diphenylethanols via a New Stereodivergent Opening of trans-1,2-Diphenyloxirane

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-diphenylethano...

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Veröffentlicht in:Journal of organic chemistry 2003-04, Vol.68 (8), p.3360-3362
Hauptverfasser: LUPATTELLI, Paolo, BONINI, Carlo, CARUSO, Leonilde, GAMBACORTA, Augusto
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034133p