Copper(II) Chloride Mediated Racemization-Free Hydrolysis of α-Alkylated Ketone Samp-Hydrazones

Treatment of ketone SAMP-hydrazones la-k with an aqueous copper(II) chloride solution yields the corresponding ketones 2a-k in 52-94% yield and with high enantiomeric purities (ee = 89-99%). The cleavage conditions do not affect functionalities sensitive to oxidation and strong acids. The alkylation...

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Bibliographic Details
Published inSynthetic communications Vol. 29; no. 1; pp. 27 - 33
Main Authors Enders, Dieter, Hundertmark, Thomas, Lazny, Ryszard
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.01.1999
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Treatment of ketone SAMP-hydrazones la-k with an aqueous copper(II) chloride solution yields the corresponding ketones 2a-k in 52-94% yield and with high enantiomeric purities (ee = 89-99%). The cleavage conditions do not affect functionalities sensitive to oxidation and strong acids. The alkylation/cleavage protocol can be carried out in 'one-pot'.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919908085731