TY - JOUR
T1 - Chiral Silver Complex-Catalyzed Asymmetric Conjugate Addition of 1-Pyrroline-5-Carbonitrile to α-Enones
AU - Araki, Haruna
AU - Furuya, Shohei
AU - Kanemoto, Kazuya
AU - Fukuzawa, Shin Ichi
N1 - Funding Information:
The authors acknowledge financial support from the Japan Society for the Promotion of Science (JSPS) Grant-in-Aid for Scientific Research C (no. JP21K05415, S. F.) and JSPS Research Fellows (no. JP22J14694, S. F.).
Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/1/20
Y1 - 2023/1/20
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.2c02315
DO - 10.1021/acs.joc.2c02315
M3 - Article
AN - SCOPUS:85146182407
SN - 0022-3263
VL - 88
SP - 924
EP - 932
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -