Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis.Org Biomol Chem. 2016 Dec 28; 14(48):11454-11461.OB
Abstract
A series of thiourea based bifunctional organocatalysts having d-glucose as a core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (<95%), diastereoselectivities (<99%), and yields (<99%) were attained under solvent free conditions using 10 mol% of 1d0. The obtained results were explained through DFT calculations using the B3LYP/6-311G(d,p)//B3LYP/6-31G(d) basic set. The QM/MM calculations revealed the role of cyclohexanone as a solvent as well as reactant in the rate determining step imparting 31.91 kcal mol-1 of energy towards the product formation.
MeSH
Pub Type(s)
Journal Article
Language
eng
PubMed ID
27883153
Citation
Azad, Chandra S., et al. "Organocatalyzed Asymmetric Michael Addition By an Efficient Bifunctional Carbohydrate-thiourea Hybrid With Mechanistic DFT Analysis." Organic & Biomolecular Chemistry, vol. 14, no. 48, 2016, pp. 11454-11461.
Azad CS, Khan IA, Narula AK. Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis. Org Biomol Chem. 2016;14(48):11454-11461.
Azad, C. S., Khan, I. A., & Narula, A. K. (2016). Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis. Organic & Biomolecular Chemistry, 14(48), 11454-11461.
Azad CS, Khan IA, Narula AK. Organocatalyzed Asymmetric Michael Addition By an Efficient Bifunctional Carbohydrate-thiourea Hybrid With Mechanistic DFT Analysis. Org Biomol Chem. 2016 Dec 28;14(48):11454-11461. PubMed PMID: 27883153.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis.
AU - Azad,Chandra S,
AU - Khan,Imran A,
AU - Narula,Anudeep K,
Y1 - 2016/11/24/
PY - 2016/11/25/pubmed
PY - 2018/1/24/medline
PY - 2016/11/25/entrez
SP - 11454
EP - 11461
JF - Organic & biomolecular chemistry
JO - Org Biomol Chem
VL - 14
IS - 48
N2 - A series of thiourea based bifunctional organocatalysts having d-glucose as a core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (<95%), diastereoselectivities (<99%), and yields (<99%) were attained under solvent free conditions using 10 mol% of 1d0. The obtained results were explained through DFT calculations using the B3LYP/6-311G(d,p)//B3LYP/6-31G(d) basic set. The QM/MM calculations revealed the role of cyclohexanone as a solvent as well as reactant in the rate determining step imparting 31.91 kcal mol-1 of energy towards the product formation.
SN - 1477-0539
UR - https://www.unboundmedicine.com/medline/citation/27883153/Organocatalyzed_asymmetric_Michael_addition_by_an_efficient_bifunctional_carbohydrate_thiourea_hybrid_with_mechanistic_DFT_analysis_
DB - PRIME
DP - Unbound Medicine
ER -
