Asymmetric Conjugate Addition of Malonate Esters to α,β‐Unsaturated  N ‐Sulfonyl Imines: An Expeditious Route to Chiral δ‐Aminoesters and Piperidones | Zendy

Espinosa Miguel | Zendy; Blay Gonzalo | Zendy; Cardona Luz | Zendy; Pedro José R. | Zendy

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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

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.

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