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Novel ferrocene-based bifunctional amine-thioureas for asymmetric Michael addition of acetylacetone to nitroolefins.
Org Biomol Chem. 2015 May 07; 13(17):5054-60.OB

Abstract

An efficient method was developed to synthesize ferrocene-based bifunctional amine-thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities. Multiple hydrogen-bonds play an important role in accelerating the reaction.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Ren X
Key Laboratory of Applied Surface and Colloid Chemistry, School of Chemistry and Chemical Engineering Shaanxi Normal University, Xi'an, Shaanxi 710062, P.R. China. ychai@snnu.edu.cn.
He C
No affiliation info available
Feng Y
No affiliation info available
Chai Y
No affiliation info available
Yao W
No affiliation info available
Chen W
No affiliation info available
Zhang S
No affiliation info available

MeSH

AlkenesAminesFerrous CompoundsHydrogen BondingMetallocenesMolecular StructureNitro CompoundsPentanonesStereoisomerismThiourea

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25832649

Citation

Ren, Xiaochen, et al. "Novel Ferrocene-based Bifunctional Amine-thioureas for Asymmetric Michael Addition of Acetylacetone to Nitroolefins." Organic & Biomolecular Chemistry, vol. 13, no. 17, 2015, pp. 5054-60.
Ren X, He C, Feng Y, et al. Novel ferrocene-based bifunctional amine-thioureas for asymmetric Michael addition of acetylacetone to nitroolefins. Org Biomol Chem. 2015;13(17):5054-60.
Ren, X., He, C., Feng, Y., Chai, Y., Yao, W., Chen, W., & Zhang, S. (2015). Novel ferrocene-based bifunctional amine-thioureas for asymmetric Michael addition of acetylacetone to nitroolefins. Organic & Biomolecular Chemistry, 13(17), 5054-60. https://doi.org/10.1039/c5ob00298b
Ren X, et al. Novel Ferrocene-based Bifunctional Amine-thioureas for Asymmetric Michael Addition of Acetylacetone to Nitroolefins. Org Biomol Chem. 2015 May 7;13(17):5054-60. PubMed PMID: 25832649.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel ferrocene-based bifunctional amine-thioureas for asymmetric Michael addition of acetylacetone to nitroolefins. AU - Ren,Xiaochen, AU - He,Chunyan, AU - Feng,Yingle, AU - Chai,Yonghai, AU - Yao,Wei, AU - Chen,Weiping, AU - Zhang,Shengyong, PY - 2015/4/3/entrez PY - 2015/4/3/pubmed PY - 2015/12/17/medline SP - 5054 EP - 60 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 17 N2 - An efficient method was developed to synthesize ferrocene-based bifunctional amine-thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities. Multiple hydrogen-bonds play an important role in accelerating the reaction. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/25832649/Novel_ferrocene_based_bifunctional_amine_thioureas_for_asymmetric_Michael_addition_of_acetylacetone_to_nitroolefins_ DB - PRIME DP - Unbound Medicine ER -