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Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.

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.

SUBMITTER: Lu C

PROVIDER: S-EPMC2980567 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.

Lu Chunliang C Xiao Qing Q Floreancig Paul E PE

Organic letters 20101020 22

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. ...[more]

PMID: 20961073

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