Catalytic enantioselective aza-Henry reaction with broad substrate scope.J Am Chem Soc. 2005 Dec 21; 127(50):17622-3.JA
Abstract
In situ generated azomethines from readily available precursors react with nitromethane in the presence of 120 mol % of CsOH.H2O and 12 mol % of quinine- and cinchonidine-derived quaternary ammonium chlorides to provide the corresponding aza-Henry adducts in good yields and very high selectivities. It represents the first general enantioselective aza-Henry method for azomethines derived from enolizable aldehydes, giving rise to enantiomeric excesses above 94%. In addition, the reactions with nitroethane afforded high diastereo- and enantioselectivities (syn:anti up to 95:5; up to 98% ee for syn).
Pub Type(s)
Journal Article
Language
eng
PubMed ID
16351089
Citation
Palomo, Claudio, et al. "Catalytic Enantioselective aza-Henry Reaction With Broad Substrate Scope." Journal of the American Chemical Society, vol. 127, no. 50, 2005, pp. 17622-3.
Palomo C, Oiarbide M, Laso A, et al. Catalytic enantioselective aza-Henry reaction with broad substrate scope. J Am Chem Soc. 2005;127(50):17622-3.
Palomo, C., Oiarbide, M., Laso, A., & López, R. (2005). Catalytic enantioselective aza-Henry reaction with broad substrate scope. Journal of the American Chemical Society, 127(50), 17622-3.
Palomo C, et al. Catalytic Enantioselective aza-Henry Reaction With Broad Substrate Scope. J Am Chem Soc. 2005 Dec 21;127(50):17622-3. PubMed PMID: 16351089.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Catalytic enantioselective aza-Henry reaction with broad substrate scope.
AU - Palomo,Claudio,
AU - Oiarbide,Mikel,
AU - Laso,Antonio,
AU - López,Rosa,
PY - 2005/12/15/pubmed
PY - 2005/12/15/medline
PY - 2005/12/15/entrez
SP - 17622
EP - 3
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 127
IS - 50
N2 - In situ generated azomethines from readily available precursors react with nitromethane in the presence of 120 mol % of CsOH.H2O and 12 mol % of quinine- and cinchonidine-derived quaternary ammonium chlorides to provide the corresponding aza-Henry adducts in good yields and very high selectivities. It represents the first general enantioselective aza-Henry method for azomethines derived from enolizable aldehydes, giving rise to enantiomeric excesses above 94%. In addition, the reactions with nitroethane afforded high diastereo- and enantioselectivities (syn:anti up to 95:5; up to 98% ee for syn).
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/16351089/Catalytic_enantioselective_aza_Henry_reaction_with_broad_substrate_scope_
DB - PRIME
DP - Unbound Medicine
ER -
