ISSN:
0947-3440
Keywords:
4,5,6-Tri- and 6-monosubstituted piperidin-2-ones
;
SAMP/RAMP hydrazone method
;
Michael additions
;
Alkylative aldehyde amination
;
Lactams
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A convenient, versatile and highly diastereo- and enantioselective synthesis of 4,5,6-trisubstituted piperidin-2-ones 1 in satisfactory overall yields is described. The procedure involves the efficient and highly anti-diastereo- and enantioselective Michael addition of aldehydes to enoates via their lithiated SAMP hydrazones, followed by nucleophilic 1,2-addition of organometallic reagents to the C=N double bond of the corresponding aldehyde SAMP hydrazone-lithium ester enolate and subsequent lactamisation. In addition, 6-monosubstituted piperidin-2-ones 8 are prepared with enantiomeric excesses of ee = 79-92% via a similar three-step sequence starting from ethyl 5-oxovalerate (9).
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970610
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