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Efficient Catalytic Corey–Chaykovsky Reactions Involving Ketone Substrates
Author(s) -
Kavanagh Sarah A.,
Piccinini Alessandro,
Con Stephen J.
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000255
Subject(s) - chemistry , ketone , catalysis , trifluoromethanesulfonate , sulfide , organic chemistry , methylene , trifluoromethyl , methyl ketone , organic base , alkyl
It has been demonstrated for the first time that a sulfide catalyst, utilised at 20 mol% loading, can promote methylene transfer to ketones in the presence of methyl triflate and an organic base. This metal‐free methodology is of broad scope – both aliphatic and aromatic ketones (including trifluoromethyl ketones) can be converted to synthetically useful terminal epoxides in excellent yields at room temperature.