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Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

ABSTRACT: Direct C(6) alkylation of pyridyl alcohols can be achieved following an initial deprotonation of the hydroxy group. This transformation, which is believed to occur by a Chichibabin-type alkylation, avoids lateral deprotonation prior to pyridine ring alkylation and gives increased regioselectivity for C(6) over C(4) alkylation.

SUBMITTER: Jeffrey JL 

PROVIDER: S-EPMC3503527 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

Jeffrey Jenna L JL   Sarpong Richmond R  

Organic letters 20121012 21

Direct C(6) alkylation of pyridyl alcohols can be achieved following an initial deprotonation of the hydroxy group. This transformation, which is believed to occur by a Chichibabin-type alkylation, avoids lateral deprotonation prior to pyridine ring alkylation and gives increased regioselectivity for C(6) over C(4) alkylation. ...[more]

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