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Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitrostyrenes.

ABSTRACT: A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate-phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

SUBMITTER: Motevalli S

PROVIDER: S-EPMC8278291 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitrostyrenes.

Motevalli Somayeh S Johnson Jeffrey S JS

Synthesis 20170502 12

A new reductive coupling reaction between <i>N</i>-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate-phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction wit ...[more]

PMID: 34267406

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