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Highly enantioselective synthesis of alpha-stereogenic esters through catalytic asymmetric michael addition of 4-oxo-4-arylbutenoates.
Chemistry. 2010 Sep 03; 16(33):10130-6.C

Abstract

Highly enantioselective Michael addition of 1,3-dicarbonyl compounds and nitromethane to 4-oxo-4-arylbutenoates catalyzed by N,N'-dioxide-Sc(OTf)(3) complexes has been developed. Using 0.5-2 mol % catalyst loading, various alpha-stereogenic esters were obtained regioselectively with excellent yields (up to 97 %) and enantioselectivities (up to >99 % ee). Moreover, the reaction performed well under nearly solvent-free conditions. The products with functional groups are ready for further transformation, which showed the potential value of the catalytic approach. According to the experimental results and previous reports, a plausible working model has been proposed to explain the origin of the activation and the asymmetric induction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang Z
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Chen D
No affiliation info available
Yang Z
No affiliation info available
Bai S
No affiliation info available
Liu X
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

MeSH

AlkenesButyratesCatalysisEstersMesylatesMolecular ConformationMolecular StructureScandiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20645351

Citation

Wang, Zhen, et al. "Highly Enantioselective Synthesis of Alpha-stereogenic Esters Through Catalytic Asymmetric Michael Addition of 4-oxo-4-arylbutenoates." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 16, no. 33, 2010, pp. 10130-6.
Wang Z, Chen D, Yang Z, et al. Highly enantioselective synthesis of alpha-stereogenic esters through catalytic asymmetric michael addition of 4-oxo-4-arylbutenoates. Chemistry. 2010;16(33):10130-6.
Wang, Z., Chen, D., Yang, Z., Bai, S., Liu, X., Lin, L., & Feng, X. (2010). Highly enantioselective synthesis of alpha-stereogenic esters through catalytic asymmetric michael addition of 4-oxo-4-arylbutenoates. Chemistry (Weinheim an Der Bergstrasse, Germany), 16(33), 10130-6. https://doi.org/10.1002/chem.201001129
Wang Z, et al. Highly Enantioselective Synthesis of Alpha-stereogenic Esters Through Catalytic Asymmetric Michael Addition of 4-oxo-4-arylbutenoates. Chemistry. 2010 Sep 3;16(33):10130-6. PubMed PMID: 20645351.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective synthesis of alpha-stereogenic esters through catalytic asymmetric michael addition of 4-oxo-4-arylbutenoates. AU - Wang,Zhen, AU - Chen,Donghui, AU - Yang,Zhigang, AU - Bai,Sha, AU - Liu,Xiaohua, AU - Lin,Lili, AU - Feng,Xiaoming, PY - 2010/7/21/entrez PY - 2010/7/21/pubmed PY - 2011/2/12/medline SP - 10130 EP - 6 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 16 IS - 33 N2 - Highly enantioselective Michael addition of 1,3-dicarbonyl compounds and nitromethane to 4-oxo-4-arylbutenoates catalyzed by N,N'-dioxide-Sc(OTf)(3) complexes has been developed. Using 0.5-2 mol % catalyst loading, various alpha-stereogenic esters were obtained regioselectively with excellent yields (up to 97 %) and enantioselectivities (up to >99 % ee). Moreover, the reaction performed well under nearly solvent-free conditions. The products with functional groups are ready for further transformation, which showed the potential value of the catalytic approach. According to the experimental results and previous reports, a plausible working model has been proposed to explain the origin of the activation and the asymmetric induction. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/20645351/Highly_enantioselective_synthesis_of_alpha_stereogenic_esters_through_catalytic_asymmetric_michael_addition_of_4_oxo_4_arylbutenoates_ L2 - https://doi.org/10.1002/chem.201001129 DB - PRIME DP - Unbound Medicine ER -