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. 2010 Nov 19;12(22):5112-5.
doi: 10.1021/ol102246d. Epub 2010 Oct 20.

Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation

Chunliang Lu  1 , Qing Xiao, Paul E Floreancig
Affiliations

Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation

Chunliang Lu et al. Org Lett. .

Abstract

Spirooxindole amides can be prepared by the intramolecular addition of functionalized indoles into acylimines that are accessed from nitriles by hydrozirconation and acylation. The stereochemical outcome at the quaternary center was controlled by the steric bulk of the substituent at the 2-position of the indole unit. The products are well-suited for diversification to prepare libraries.

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Figures

Scheme 1
Scheme 1
Spirooxindole formation through acylimine addition.
Scheme 2
Scheme 2
Substrate synthesis.
Scheme 3
Scheme 3
Oxindole formation through nitrile hydrozirconation, acylation, and intramolecular addition.
Scheme 4
Scheme 4
Spirooxindole functionalizations.
See this image and copyright information in PMC

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