Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst.Org Biomol Chem. 2010 Jan 07; 8(1):77-82.OB
Abstract
The current article reports an organocatalytic strategy for the asymmetric catalysis of chiral oxindoles bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted oxindoles to terminal alkenes have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of Michael donor compounds (different substituted 3-aryl or methyl oxindoles), and Michael acceptor compounds (vinyl ketones and vinyl sulfones) to give the desired oxindole products with moderate to excellent yields (up to 99%) and moderate to excellent enantioselectivities (up to 91% ee).
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
20024135
Citation
Li, Xin, et al. "Asymmetric Michael Addition Reaction of 3-substituted-N-Boc Oxindoles to Activated Terminal Alkenes Catalyzed By a Bifunctional Tertiary-amine Thiourea Catalyst." Organic & Biomolecular Chemistry, vol. 8, no. 1, 2010, pp. 77-82.
Li X, Xi ZG, Luo S, et al. Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst. Org Biomol Chem. 2010;8(1):77-82.
Li, X., Xi, Z. G., Luo, S., & Cheng, J. P. (2010). Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst. Organic & Biomolecular Chemistry, 8(1), 77-82. https://doi.org/10.1039/b918644a
Li X, et al. Asymmetric Michael Addition Reaction of 3-substituted-N-Boc Oxindoles to Activated Terminal Alkenes Catalyzed By a Bifunctional Tertiary-amine Thiourea Catalyst. Org Biomol Chem. 2010 Jan 7;8(1):77-82. PubMed PMID: 20024135.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst.
AU - Li,Xin,
AU - Xi,Zhi-Guo,
AU - Luo,Sanzhong,
AU - Cheng,Jin-Pei,
Y1 - 2009/10/29/
PY - 2009/12/22/entrez
PY - 2009/12/22/pubmed
PY - 2009/12/22/medline
SP - 77
EP - 82
JF - Organic & biomolecular chemistry
JO - Org Biomol Chem
VL - 8
IS - 1
N2 - The current article reports an organocatalytic strategy for the asymmetric catalysis of chiral oxindoles bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted oxindoles to terminal alkenes have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of Michael donor compounds (different substituted 3-aryl or methyl oxindoles), and Michael acceptor compounds (vinyl ketones and vinyl sulfones) to give the desired oxindole products with moderate to excellent yields (up to 99%) and moderate to excellent enantioselectivities (up to 91% ee).
SN - 1477-0539
UR - https://www.unboundmedicine.com/medline/citation/20024135/Asymmetric_Michael_addition_reaction_of_3_substituted_N_Boc_oxindoles_to_activated_terminal_alkenes_catalyzed_by_a_bifunctional_tertiary_amine_thiourea_catalyst_
L2 - https://doi.org/10.1039/b918644a
DB - PRIME
DP - Unbound Medicine
ER -
