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Scandium(III)-catalyzed enantioselective allylation of isatins using allylsilanes.
Org Lett. 2012 May 04; 14(9):2218-21.OL

Abstract

The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hanhan NV
Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States.
Tang YC
No affiliation info available
Tran NT
No affiliation info available
Franz AK
No affiliation info available

MeSH

CatalysisHydrocarbons, HalogenatedIsatinMolecular StructureScandiumSilanesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

22506841

Citation

Hanhan, Nadine V., et al. "Scandium(III)-catalyzed Enantioselective Allylation of Isatins Using Allylsilanes." Organic Letters, vol. 14, no. 9, 2012, pp. 2218-21.
Hanhan NV, Tang YC, Tran NT, et al. Scandium(III)-catalyzed enantioselective allylation of isatins using allylsilanes. Org Lett. 2012;14(9):2218-21.
Hanhan, N. V., Tang, Y. C., Tran, N. T., & Franz, A. K. (2012). Scandium(III)-catalyzed enantioselective allylation of isatins using allylsilanes. Organic Letters, 14(9), 2218-21. https://doi.org/10.1021/ol300496v
Hanhan NV, et al. Scandium(III)-catalyzed Enantioselective Allylation of Isatins Using Allylsilanes. Org Lett. 2012 May 4;14(9):2218-21. PubMed PMID: 22506841.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Scandium(III)-catalyzed enantioselective allylation of isatins using allylsilanes. AU - Hanhan,Nadine V, AU - Tang,Yng C, AU - Tran,Ngon T, AU - Franz,Annaliese K, Y1 - 2012/04/16/ PY - 2012/4/18/entrez PY - 2012/4/18/pubmed PY - 2012/7/26/medline SP - 2218 EP - 21 JF - Organic letters JO - Org Lett VL - 14 IS - 9 N2 - The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22506841/Scandium_III__catalyzed_enantioselective_allylation_of_isatins_using_allylsilanes_ L2 - https://doi.org/10.1021/ol300496v DB - PRIME DP - Unbound Medicine ER -