Highly Regioselective C(3) Opening of an Aromatic 2,3-Epoxy Alcohol with Sodium Phenoxides or Thiophenoxides (=Benzenethiolates) Supported by β-Cyclodextrin in Water

A simple and mild procedure was developed for the first time for the C(3)‐selective ring opening of an aromatic 2,3‐epoxy alcohol, i.e., of trans‐3‐phenyloxirane‐2‐methanol (1), with sodium phenoxides or thiophenoxides (=benzenethiolates) 2 supported by β‐cyclodextrin in H2O at 50° to afford the cor...

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Veröffentlicht in:	Helvetica chimica acta 2007-06, Vol.90 (6), p.1107-1111
Hauptverfasser:	Narender, Mendu, Reddy, Majjigapu Somi, Nageswar, Yadavalli Venkata Durga, Rao, Kakulapati Rama
Format:	Artikel
Sprache:	eng
Schlagworte:	2-diol 3-epoxy Alcohol Alcohol, 2,3‐epoxy Benzenethiolates Cyclodextrins Phenoxide Phenoxide, sodium salt Propane-1 Propane‐1,2‐diol Ring-opening reaction sodium salt Thiophenoxide
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Beschreibung
Zusammenfassung:	A simple and mild procedure was developed for the first time for the C(3)‐selective ring opening of an aromatic 2,3‐epoxy alcohol, i.e., of trans‐3‐phenyloxirane‐2‐methanol (1), with sodium phenoxides or thiophenoxides (=benzenethiolates) 2 supported by β‐cyclodextrin in H2O at 50° to afford the corresponding 3‐(aryloxy)‐ or 3‐(arylthio)propane1,2‐diols 3 in excellent yields (Scheme, Table).
ISSN:	0018-019X 1522-2675
DOI:	10.1002/hlca.200790109