Premium
Asymmetric Conjugate Addition of Malonate Esters to α,β‐Unsaturated N ‐Sulfonyl Imines: An Expeditious Route to Chiral δ‐Aminoesters and Piperidones
Author(s) -
Espinosa Miguel,
Blay Gonzalo,
Cardona Luz,
Pedro José R.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302687
Subject(s) - stereocenter , malonate , sulfonyl , conjugate , chemistry , allylic rearrangement , medicinal chemistry , enantiomer , diethyl malonate , addition reaction , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , mathematics , mathematical analysis , alkyl
Abstract The asymmetric conjugate addition of malonate esters to α,β‐unsaturated N ‐sulfonyl imines is catalyzed by PyBOX/La(OTf) 3 complexes in the presence of 4 Å MS. The reaction gives the corresponding E enamines bearing a stereogenic center at the allylic position with good yields and enantiomeric ratios up to 97:3. This reaction provides a synthetic entry to chiral δ‐aminoesters and piperidones.