Synthesis of phenol derivatives from cyclohex-2-enones bearing an alkyne through Lewis acid-catalyzed enolization and intramolecular Alder-Rickert reaction

Atsushi Kinbara; Takehiro Yamagishi; Naoko Hanzawa; Etsuko Kawashima; Hiroaki Miyaoka

doi:10.1021/jo301554z

Synthesis of phenol derivatives from cyclohex-2-enones bearing an alkyne through Lewis acid-catalyzed enolization and intramolecular Alder-Rickert reaction

J Org Chem. 2012 Oct 19;77(20):8999-9005. doi: 10.1021/jo301554z. Epub 2012 Oct 4.

Authors

Atsushi Kinbara¹, Takehiro Yamagishi, Naoko Hanzawa, Etsuko Kawashima, Hiroaki Miyaoka

Affiliation

¹ School of Pharmaceutical Sciences, Ohu University, Misumido 31-1, Tomita-machi, Koriyama, Fukushima 963-8611, Japan.

PMID: 23003109
DOI: 10.1021/jo301554z

Abstract

A cationic rhodium(I) complex- or In(OTf)(3)-catalyzed synthesis of phenol derivatives from cyclohex-2-enone having an ethoxycarbonyl-substituted alkyne has been achieved. This reaction proceeds via enolization and an intramolecular Alder-Rickert reaction.

MeSH terms

Catalysis
Cyclohexanones / chemistry*
Lewis Acids / chemistry*
Mesylates / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Phenols / chemical synthesis*
Phenols / chemistry
Rhodium / chemistry*

Substances

Cyclohexanones
Lewis Acids
Mesylates
Organometallic Compounds
Phenols
Rhodium
trifluoromethanesulfonic acid