A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione® Precursor

Dehydrohedione (DHH) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a, by treatment with CuBr2, in MeOH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX2 Kochi's conditions goes preferentially throug...

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Bibliographic Details
Published in:Helvetica chimica acta 2018-08, Vol.101 (8), p.n/a
Main Authors: Chapuis, Christian, Richard, Claude‐Alain
Format: Article
Language:English
Subjects:
Copper bromide
cupric malonate
decarbomethoxylation
Halogenation
Hedione
Intermediates
Refluxing
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Summary:Dehydrohedione (DHH) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a, by treatment with CuBr2, in MeOH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX2 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 CuX2, while in‐situ decarbomethoxylation is promoted by the resulting CuX in refluxing MeOH.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201800063