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Diastereo‐ and Enantioselective Synthesis of 4,5,6‐Trisubstituted and 6‐Monosubstituted Piperidin‐2‐ones
Author(s) -
Enders Dieter,
Bartzen Dominika
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970610
Subject(s) - enantioselective synthesis , chemistry , aldehyde , hydrazone , reagent , enantiomer , lithium (medication) , nucleophile , stereochemistry , michael reaction , organic chemistry , catalysis , medicine , endocrinology
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 CN 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 ).