Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of lithium dimethylcuprate to ζ‐Oxo‐α, β‐enones preliminary communication [1] | Zendy

Näf Ferdinand | Zendy; Decorzant René | Zendy; Thommen Walter | Zendy

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Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of lithium dimethylcuprate to ζ‐Oxo‐α, β‐enones preliminary communication [1]

Author(s) -

Näf Ferdinand,

Decorzant René,

Thommen Walter

Publication year - 1975

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.19750580635

Subject(s) - chemistry , conjugate , intramolecular force , aldol condensation , lithium (medication) , stereospecificity , aldol reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , mathematical analysis , mathematics , endocrinology

ζ‐Oxo‐α, β‐enones react with lithium dimethylcuprate to give cyclic aldols such as hydroxydecalone 1 and hydroxyspiro[4.5]decanone 2 in a regio‐ and stereospecific manner. This new reaction, a combination of conjugate methyl addition to α, β‐enones with directed intramolecular aldolisation, is suggested to proceed via either enoate anions, such as 8 and 11 , or radical anions, such as 9 → 10 and 12 → 13 , as intermediates.

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