Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: Synthesis of spirooxindoles

Nadine V. Hanhan; Nicolas R. Ball-Jones; Ngon T. Tran; Annaliese K. Franz

doi:10.1002/anie.201105739

Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: Synthesis of spirooxindoles

Nadine V. Hanhan, Nicolas R. Ball-Jones, Ngon T. Tran, Annaliese K. Franz

Research output: Contribution to journal › Article › peer-review

120 Scopus citations

Abstract

Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl ₂(SbF ₆)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si-C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.

Original language	English (US)
Pages (from-to)	989-992
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	4
DOIs	https://doi.org/10.1002/anie.201105739
State	Published - Jan 23 2012
Externally published	Yes

Keywords

allylic compounds
annulation
asymmetric catalysis
enantioselectivity
scandium

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10.1002/anie.201105739

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abstract = "Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl 2(SbF 6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si-C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.",

keywords = "allylic compounds, annulation, asymmetric catalysis, enantioselectivity, scandium",

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T1 - Catalytic asymmetric [3+2] annulation of allylsilanes with isatins

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AU - Hanhan, Nadine V.

AU - Ball-Jones, Nicolas R.

AU - Tran, Ngon T.

AU - Franz, Annaliese K.

PY - 2012/1/23

Y1 - 2012/1/23

N2 - Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl 2(SbF 6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si-C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.

AB - Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl 2(SbF 6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si-C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.

KW - allylic compounds

KW - annulation

KW - asymmetric catalysis

KW - enantioselectivity

KW - scandium

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ER -

Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: Synthesis of spirooxindoles

Abstract

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