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Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles].
J Org Chem. 2015 Jun 05; 80(11):5951-7.JO

Abstract

An efficient and unprecedented organocatalytic asymmetric reaction of 3-pyrrolyl-oxindoles with α,β-unsaturated aldehydes to generate spirocyclic oxindole compounds was developed. The reactions were catalyzed by diphenylprolinol silyl ether and 2-fluorobenzoic acid via an asymmetric Michael/Friedel-Crafts cascade process, followed by dehydration with p-toluenesulfonic acid to afford a wide variety of structurally diverse spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindole] derivatives in high yields (up to 93%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee).

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Authors+Show Affiliations

You Y
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. §University of Chinese Academy of Sciences, Beijing 10049, China.
Cui BD
‡School of Pharmacy, Zunyi Medical University, Zunyi 563000, China.
Zhou MQ
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. §University of Chinese Academy of Sciences, Beijing 10049, China.
Zuo J
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. §University of Chinese Academy of Sciences, Beijing 10049, China.
Zhao JQ
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. §University of Chinese Academy of Sciences, Beijing 10049, China.
Xu XY
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Zhang XM
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Yuan WC
†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

MeSH

AldehydesCatalysisIndolesMolecular StructureOxindolesPyrrolesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

25984596

Citation

You, Yong, et al. "Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles]." The Journal of Organic Chemistry, vol. 80, no. 11, 2015, pp. 5951-7.
You Y, Cui BD, Zhou MQ, et al. Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles]. J Org Chem. 2015;80(11):5951-7.
You, Y., Cui, B. D., Zhou, M. Q., Zuo, J., Zhao, J. Q., Xu, X. Y., Zhang, X. M., & Yuan, W. C. (2015). Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles]. The Journal of Organic Chemistry, 80(11), 5951-7. https://doi.org/10.1021/acs.joc.5b00597
You Y, et al. Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles]. J Org Chem. 2015 Jun 5;80(11):5951-7. PubMed PMID: 25984596.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles]. AU - You,Yong, AU - Cui,Bao-Dong, AU - Zhou,Ming-Qiang, AU - Zuo,Jian, AU - Zhao,Jian-Qiang, AU - Xu,Xiao-Ying, AU - Zhang,Xiao-Mei, AU - Yuan,Wei-Cheng, Y1 - 2015/05/26/ PY - 2015/5/19/entrez PY - 2015/5/20/pubmed PY - 2016/2/26/medline SP - 5951 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 80 IS - 11 N2 - An efficient and unprecedented organocatalytic asymmetric reaction of 3-pyrrolyl-oxindoles with α,β-unsaturated aldehydes to generate spirocyclic oxindole compounds was developed. The reactions were catalyzed by diphenylprolinol silyl ether and 2-fluorobenzoic acid via an asymmetric Michael/Friedel-Crafts cascade process, followed by dehydration with p-toluenesulfonic acid to afford a wide variety of structurally diverse spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindole] derivatives in high yields (up to 93%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/25984596/Organocatalytic_Asymmetric_Michael/Friedel_Crafts_Cascade_Reaction_of_3_Pyrrolyl_oxindoles_and_αβ_Unsaturated_Aldehydes_for_the_Construction_of_Chiral_Spiro[56_dihydropyrido[12_a]pyrrole_33'_oxindoles]_ DB - PRIME DP - Unbound Medicine ER -