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Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives.
Chem Asian J. 2013 May; 8(5):883-7.CA

Abstract

A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Peng JB
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P R China.
Qi Y
No affiliation info available
Ma AJ
No affiliation info available
Tu YQ
No affiliation info available
Zhang FM
No affiliation info available
Wang SH
No affiliation info available
Zhang SY
No affiliation info available

MeSH

AziridinesCrystallography, X-RayCyclobutanesIndolesModels, MolecularMolecular StructureOxidation-ReductionOxindolesSpiro Compounds

Pub Type(s)

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

Language

eng

PubMed ID

23423783

Citation

Peng, Jin-Bao, et al. "Cascade Oxidative Dearomatization/semipinacol Rearrangement: an Approach to 2-spirocyclo-3-oxindole Derivatives." Chemistry, an Asian Journal, vol. 8, no. 5, 2013, pp. 883-7.
Peng JB, Qi Y, Ma AJ, et al. Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives. Chem Asian J. 2013;8(5):883-7.
Peng, J. B., Qi, Y., Ma, A. J., Tu, Y. Q., Zhang, F. M., Wang, S. H., & Zhang, S. Y. (2013). Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives. Chemistry, an Asian Journal, 8(5), 883-7. https://doi.org/10.1002/asia.201300032
Peng JB, et al. Cascade Oxidative Dearomatization/semipinacol Rearrangement: an Approach to 2-spirocyclo-3-oxindole Derivatives. Chem Asian J. 2013;8(5):883-7. PubMed PMID: 23423783.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives. AU - Peng,Jin-Bao, AU - Qi,Yue, AU - Ma,Ai-Jun, AU - Tu,Yong-Qiang, AU - Zhang,Fu-Min, AU - Wang,Shao-Hua, AU - Zhang,Shu-Yu, Y1 - 2013/02/19/ PY - 2013/01/09/received PY - 2013/2/21/entrez PY - 2013/2/21/pubmed PY - 2014/1/22/medline SP - 883 EP - 7 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 8 IS - 5 N2 - A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/23423783/Cascade_oxidative_dearomatization/semipinacol_rearrangement:_an_approach_to_2_spirocyclo_3_oxindole_derivatives_ L2 - https://doi.org/10.1002/asia.201300032 DB - PRIME DP - Unbound Medicine ER -