Chiral Silver Complex-Catalyzed Asymmetric Conjugate Addition of 1‑Pyrroline-5-Carbonitrile to α‑Enones

The conjugated addition reaction of 1-pyrroline-5-carbonitrile to α-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether in the presence of 1,8-diazabicyclo[5.4.0]­undec-7-ene (DBU), and nearly single diastereomers of adducts with good enantiomeric excesses (up to 97% ee...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-01, Vol.88 (2), p.924-932
Main Authors: Araki, Haruna, Furuya, Shohei, Kanemoto, Kazuya, Fukuzawa, Shin-ichi
Format: Article
Language:English
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Summary:The conjugated addition reaction of 1-pyrroline-5-carbonitrile to α-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether in the presence of 1,8-diazabicyclo[5.4.0]­undec-7-ene (DBU), and nearly single diastereomers of adducts with good enantiomeric excesses (up to 97% ee) were obtained in high yields. The reduction of the nitrile group with H2/Raney Ni in ethanol successfully transformed the conjugate adduct to the corresponding spirocyclic piperidine (60% yield) as a single stereoisomer.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02315