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The Reaction of Cyclopropyl Ketones with Acetyl Methanesulfonate. An efficient ring opening under neutral conditions with regiospecific enol acetate formation and stereo‐controlled nucleophilic addition. Preliminary communication
Author(s) -
Demuth Martin,
Raghavan Palaykotai R.
Publication year - 1979
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.19790620730
Subject(s) - chemistry , nucleophile , enol , stereoselectivity , yield (engineering) , ring (chemistry) , medicinal chemistry , nucleophilic addition , stereochemistry , organic chemistry , catalysis , metallurgy , materials science
Abstract Cyclopropyl ketones are readily cleaved under neutral conditions at room temperature by the combined action of acetyl methanesulfonate and nucleophiles such as Br − , I − , and MsO − . The high‐yield reaction involves regiospecific enol acetate formation with a stereoselectivity of nucleophile addition which is compatible with an S N 2‐type opening of the cyclopropyl ring.