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Stereoselective Synthesis of Chiral 2,3‐Disubstituted 2,3‐Dihydro‐4(1 H )‐pyridones
Author(s) -
Etayo Pablo,
Badorrey Ramón,
DíazdeVillegas María D.,
Gálvez José A.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800697
Subject(s) - chemistry , deprotonation , stereoselectivity , electrophile , yield (engineering) , alkylation , stereochemistry , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis , ion , materials science , metallurgy
The alkylation at C‐3 of the easily accessible ( R )‐2‐[( S )‐1,2‐bis(benzyloxy)ethyl]‐1‐[( S )‐1‐phenylethyl]‐2,3‐dihydro‐4(1 H )‐pyridone with different electrophiles took place with total trans diastereoselectivity to afford the corresponding (2 R ,3 S )‐2,3‐disubstituted 2,3‐dihydro‐4(1 H )‐pyridones in enantiomerically pure form. The configuration at C‐3 can be inverted by deprotonation and subsequent reprotonation to yield the corresponding (2 R ,3 R )‐2,3‐disubstituted 2,3‐dihydro‐4(1 H )‐pyridones in a highly diastereoselective manner.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)