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Facile Conversion of Cyclopropanols into Linear Conjugate Enones
Author(s) -
Han WeiBo,
Li ShaoGang,
Lu XiaoWei,
Wu Yikang
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402175
Subject(s) - chemistry , reagent , regioselectivity , conjugate , cyclopropanation , cyclopropane , catalysis , cleavage (geology) , organic chemistry , combinatorial chemistry , ring (chemistry) , mathematical analysis , mathematics , geotechnical engineering , fracture (geology) , engineering
A practical method for the conversion of 1,2‐disubstituted cyclopropanols derived from Kulinkovich cyclopropanation into linear enones was developed. The approach features regioselective cleavage of the cyclopropane rings in EtOH at ambient temperature with inexpensive and readily available Co(acac) 2 as the catalyst and air as the reagent. The crude intermediate peroxides were directly reduced with Ph 3 P to afford the corresponding β‐hydroxy ketones, which, on mesylation and β‐elimination performed in a one‐pot manner, furnished the end products in good to excellent yields after only one chromatography step at the end of the whole sequence.