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An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles.
Chem Commun (Camb). 2013 Oct 21; 49(82):9422-4.CC

Abstract

The first organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25-85% yield, 60-94% ee and up to >20 : 1 diastereoselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang QL
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. wlxioc@cioc.ac.cn xuxy@cioc.ac.cn.
Peng L
No affiliation info available
Wang FY
No affiliation info available
Zhang ML
No affiliation info available
Jia LN
No affiliation info available
Tian F
No affiliation info available
Xu XY
No affiliation info available
Wang LX
No affiliation info available

MeSH

AlkylationAllyl CompoundsCarbonatesCatalysisCyclizationIndolesMolecular StructureOxindolesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24005475

Citation

Wang, Qi-Lin, et al. "An Organocatalytic Asymmetric Sequential Allylic Alkylation-cyclization of Morita-Baylis-Hillman Carbonates and 3-hydroxyoxindoles." Chemical Communications (Cambridge, England), vol. 49, no. 82, 2013, pp. 9422-4.
Wang QL, Peng L, Wang FY, et al. An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles. Chem Commun (Camb). 2013;49(82):9422-4.
Wang, Q. L., Peng, L., Wang, F. Y., Zhang, M. L., Jia, L. N., Tian, F., Xu, X. Y., & Wang, L. X. (2013). An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles. Chemical Communications (Cambridge, England), 49(82), 9422-4. https://doi.org/10.1039/c3cc45139a
Wang QL, et al. An Organocatalytic Asymmetric Sequential Allylic Alkylation-cyclization of Morita-Baylis-Hillman Carbonates and 3-hydroxyoxindoles. Chem Commun (Camb). 2013 Oct 21;49(82):9422-4. PubMed PMID: 24005475.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles. AU - Wang,Qi-Lin, AU - Peng,Lin, AU - Wang,Fei-Ying, AU - Zhang,Ming-Liang, AU - Jia,Li-Na, AU - Tian,Fang, AU - Xu,Xiao-Ying, AU - Wang,Li-Xin, PY - 2013/9/6/entrez PY - 2013/9/6/pubmed PY - 2014/4/23/medline SP - 9422 EP - 4 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 49 IS - 82 N2 - The first organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25-85% yield, 60-94% ee and up to >20 : 1 diastereoselectivity. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/24005475/An_organocatalytic_asymmetric_sequential_allylic_alkylation_cyclization_of_Morita_Baylis_Hillman_carbonates_and_3_hydroxyoxindoles_ DB - PRIME DP - Unbound Medicine ER -