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Highly enantioselective allylation of alpha-ketoesters catalyzed by N,N'-dioxide-In(III) complexes.
J Org Chem. 2007 Oct 26; 72(22):8478-83.JO

Abstract

An efficient asymmetric allylation of alpha-ketoesters was catalyzed by the N,N'-dioxide-In(III) complex in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) for a variety of substrates under mild reaction conditions. On the basis of experimental results, a possible catalytic cycle including a transition state has been proposed to explain the origin of the reactivity and asymmetric inductivity, and a bifunctional catalysis was described with Lewis base N-oxide activating tetraallylstannane and Lewis acid indium activating alpha-ketoester.

Authors+Show Affiliations

Zheng K
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Qin B
No affiliation info available
Liu X
No affiliation info available
Feng X
No affiliation info available

MeSH

AlcoholsAlkylationCatalysisCombinatorial Chemistry TechniquesCyclizationEstersIndiumKetonesMolecular StructureOrganometallic CompoundsOxidesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17919001

Citation

Zheng, Ke, et al. "Highly Enantioselective Allylation of Alpha-ketoesters Catalyzed By N,N'-dioxide-In(III) Complexes." The Journal of Organic Chemistry, vol. 72, no. 22, 2007, pp. 8478-83.
Zheng K, Qin B, Liu X, et al. Highly enantioselective allylation of alpha-ketoesters catalyzed by N,N'-dioxide-In(III) complexes. J Org Chem. 2007;72(22):8478-83.
Zheng, K., Qin, B., Liu, X., & Feng, X. (2007). Highly enantioselective allylation of alpha-ketoesters catalyzed by N,N'-dioxide-In(III) complexes. The Journal of Organic Chemistry, 72(22), 8478-83.
Zheng K, et al. Highly Enantioselective Allylation of Alpha-ketoesters Catalyzed By N,N'-dioxide-In(III) Complexes. J Org Chem. 2007 Oct 26;72(22):8478-83. PubMed PMID: 17919001.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective allylation of alpha-ketoesters catalyzed by N,N'-dioxide-In(III) complexes. AU - Zheng,Ke, AU - Qin,Bo, AU - Liu,Xiaohua, AU - Feng,Xiaoming, Y1 - 2007/10/06/ PY - 2007/10/9/pubmed PY - 2008/1/8/medline PY - 2007/10/9/entrez SP - 8478 EP - 83 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 22 N2 - An efficient asymmetric allylation of alpha-ketoesters was catalyzed by the N,N'-dioxide-In(III) complex in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) for a variety of substrates under mild reaction conditions. On the basis of experimental results, a possible catalytic cycle including a transition state has been proposed to explain the origin of the reactivity and asymmetric inductivity, and a bifunctional catalysis was described with Lewis base N-oxide activating tetraallylstannane and Lewis acid indium activating alpha-ketoester. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17919001/Highly_enantioselective_allylation_of_alpha_ketoesters_catalyzed_by_NN'_dioxide_In_III__complexes_ L2 - https://doi.org/10.1021/jo701491r DB - PRIME DP - Unbound Medicine ER -