Novel bifunctional chiral thiourea catalyzed highly enantioselective aza-Henry reaction.Org Lett. 2008 May 01; 10(9):1707-10.OL
Abstract
A novel bifunctional chiral thiourea organocatalyst bearing a glycosyl scaffold and a tertiary amino group was synthesized starting from readily available alpha-D-glucose. This thiourea was proven to be an effective organocatalyst for the asymmetric aza-Henry reaction between N-Boc imines and nitromethane. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 99.8% ee). In addition, the reaction of nitroethane also proceeded smoothly with excellent enantioselectivity, albeit with low to good diastereoselectivities.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
18396893
Citation
Wang, Chungui, et al. "Novel Bifunctional Chiral Thiourea Catalyzed Highly Enantioselective aza-Henry Reaction." Organic Letters, vol. 10, no. 9, 2008, pp. 1707-10.
Wang C, Zhou Z, Tang C. Novel bifunctional chiral thiourea catalyzed highly enantioselective aza-Henry reaction. Org Lett. 2008;10(9):1707-10.
Wang, C., Zhou, Z., & Tang, C. (2008). Novel bifunctional chiral thiourea catalyzed highly enantioselective aza-Henry reaction. Organic Letters, 10(9), 1707-10. https://doi.org/10.1021/ol8003035
Wang C, Zhou Z, Tang C. Novel Bifunctional Chiral Thiourea Catalyzed Highly Enantioselective aza-Henry Reaction. Org Lett. 2008 May 1;10(9):1707-10. PubMed PMID: 18396893.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Novel bifunctional chiral thiourea catalyzed highly enantioselective aza-Henry reaction.
AU - Wang,Chungui,
AU - Zhou,Zhenghong,
AU - Tang,Chuchi,
Y1 - 2008/04/09/
PY - 2008/4/10/pubmed
PY - 2008/4/10/medline
PY - 2008/4/10/entrez
SP - 1707
EP - 10
JF - Organic letters
JO - Org Lett
VL - 10
IS - 9
N2 - A novel bifunctional chiral thiourea organocatalyst bearing a glycosyl scaffold and a tertiary amino group was synthesized starting from readily available alpha-D-glucose. This thiourea was proven to be an effective organocatalyst for the asymmetric aza-Henry reaction between N-Boc imines and nitromethane. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 99.8% ee). In addition, the reaction of nitroethane also proceeded smoothly with excellent enantioselectivity, albeit with low to good diastereoselectivities.
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/18396893/Novel_bifunctional_chiral_thiourea_catalyzed_highly_enantioselective_aza_Henry_reaction_
DB - PRIME
DP - Unbound Medicine
ER -
