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A One Pot Synthesis of Dehydrohedione ( DHH ) from a Hedione ® Precursor
Author(s) -
Chapuis Christian,
Richard ClaudeAlain
Publication year - 2018
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.201800063
Subject(s) - chemistry , dehydrohalogenation , moiety , halogenation , malonate , yield (engineering) , ketone , stereochemistry , domino , derivative (finance) , transformation (genetics) , medicinal chemistry , organic chemistry , biochemistry , catalysis , materials science , economics , financial economics , metallurgy , gene
Dehydrohedione ( DHH ) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a , by treatment with CuBr 2 , in Me OH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX 2 Kochi 's conditions goes preferentially through the pathway involving intermediates 2b / 2c and 7a , rather than 3a / 3b or 8a / 8b , essentially via α ‐halogenation/dehydrohalogenation of the ketone moiety, both mediated by CuX 2 , while in‐situ decarbomethoxylation is promoted by the resulting CuX in refluxing Me OH .
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