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Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic ?-addition of alkyllithiums to ?-aryl substituted piperidine enecarbamates.

ABSTRACT: Substituted piperidines are emerging as important medicinally-active structural motifs. Here, we report highly stereoselective carbolithiation reactions of ?-aryl piperidine enecarbamates that offer direct access to vicinally-substituted piperidine compounds. We have also demonstrated that the carbanion intermediates can be trapped with a carbon electrophile.

SUBMITTER: Beng TK

PROVIDER: S-EPMC4435544 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates.

Beng Timothy K TK Takeuchi Hironori H Weber Manuel M Sarpong Richmond R

Chemical communications (Cambridge, England) 20150501 36

Substituted piperidines are emerging as important medicinally-active structural motifs. Here, we report highly stereoselective carbolithiation reactions of α-aryl piperidine enecarbamates that offer direct access to vicinally-substituted piperidine compounds. We have also demonstrated that the carbanion intermediates can be trapped with a carbon electrophile. ...[more]

PMID: 25845938

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