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Rhenium(I)‐Catalyzed Cyclization of Silyl Enol Ethers Containing a Propargyl Carboxylate Moiety: Versatile Access to Highly Substituted Phenols
Author(s) -
Saito Kodai,
Onizawa Yuji,
Kusama Hiroyuki,
Iwasawa Nobuharu
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200903586
Subject(s) - rhenium , silylation , moiety , enol , chemistry , silyl enol ether , phenols , propargyl , nucleophile , catalysis , medicinal chemistry , carboxylate , substituent , enol ether , organic chemistry
Selective migration : The rhenium‐catalyzed reaction of 2‐siloxy‐1‐en‐5‐ynes containing an acyloxy substituent at the propargylic position gave highly substituted phenols in good yields (see scheme). Depending on the structure of the silyl enol ether, either nucleophilic addition of this moiety or 1,2‐acyloxy migration occurs to give two kinds of synthetically useful, substituted phenols.