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Highly Regioselective C(3) Opening of an Aromatic 2,3‐Epoxy Alcohol with Sodium Phenoxides or Thiophenoxides (=Benzenethiolates) Supported by β ‐Cyclodextrin in Water
Author(s) -
Narender Mendu,
Reddy Majjigapu Somi,
Nageswar Yadavalli Venkata Durga,
Rao Kakulapati Rama
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790109
Subject(s) - chemistry , regioselectivity , epoxy , methanol , alcohol , cyclodextrin , ring (chemistry) , sodium , medicinal chemistry , organic chemistry , catalysis
Abstract 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 H 2 O at 50° to afford the corresponding 3‐(aryloxy)‐ or 3‐(arylthio)propane1,2‐diols 3 in excellent yields ( Scheme, Table ).