Copper(II) chloride mediated racemization-free hydrolysis of alpha-alkylated ketone SAMP-hydrazones

Authors
Enders, D Hundertmark, T Lazny, R
Citation
D. Enders et al., Copper(II) chloride mediated racemization-free hydrolysis of alpha-alkylated ketone SAMP-hydrazones, SYN COMMUN, 29(1), 1999, pp. 27-33
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
1
Year of publication
1999
Pages
27 - 33
Database
ISI
SICI code
0039-7911(1999)29:1<27:CCMRHO>2.0.ZU;2-7
Abstract
Treatment of ketone SAMP-hydrazones 1a-k with an aqueous copper(II) chlorid e solution yields the corresponding ketones 2a-k in 52-94% yield and with h igh enantiomeric purities (ee = 89-99%). The cleavage conditions do not aff ect functionalities sensitive to oxidation and strong acids. The alkylation /cleavage protocol can be carried out in 'one-pot'.