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Palladium-catalyzed asymmetric allylic alkylation of electron-deficient pyrroles with meso electrophiles.

ABSTRACT: Pyrroles can serve as competent nucleophiles with meso electrophiles in the Pd-catalyzed asymmetric allylic alkylation. The products from this transformation were obtained as a single regio- and diastereomer in high yield and enantiopurity. A nitropyrrole-containing nucleoside analogue was synthesized in seven steps to demonstrate the synthetic utility of this transformation.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3407807 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Palladium-catalyzed asymmetric allylic alkylation of electron-deficient pyrroles with meso electrophiles.

Trost Barry M BM Osipov Maksim M Dong Guangbin G

Organic letters 20120416 9

Pyrroles can serve as competent nucleophiles with meso electrophiles in the Pd-catalyzed asymmetric allylic alkylation. The products from this transformation were obtained as a single regio- and diastereomer in high yield and enantiopurity. A nitropyrrole-containing nucleoside analogue was synthesized in seven steps to demonstrate the synthetic utility of this transformation. ...[more]

PMID: 22506671

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