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Synthesis of 1,4‐Cyclohexadiene Carboxylates through a Formal [2+4]‐Cycloaddition of Propiolates under Cobalt Catalysis
Author(s) -
Charpentier Julie,
Voirol Francis,
Flachsmann Felix,
Tanner Silvia,
Aeberli Natalie,
Brunner Gerhard,
Goeke Andreas
Publication year - 2020
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.202000175
Subject(s) - chemistry , cobalt , cycloaddition , catalysis , alkyl , aryl , combinatorial chemistry , zinc , formal synthesis , organic chemistry , medicinal chemistry
A low‐valent cobalt(I) complex, formed from the reduction of CoBr 2 (dppe) with zinc, acts as catalyst for the efficient [2+4] cycloaddition of β‐alkyl, cycloalkyl and aryl substituted propiolates to dienes. This transformation yields synthetically relevant 1,4‐cyclohexadiene carboxylates in good to excellent yields. Furthermore, the target compounds are novel lead structures for the discovery of fragrance ingredients from the fruity, floral and spicy odor family.