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Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates.

ABSTRACT: We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine.

SUBMITTER: Xu J

PROVIDER: S-EPMC2486488 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature

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Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates.

Xu Jun J Qiu Xiao-Long XL Qing Feng-Ling FL

Beilstein journal of organic chemistry 20080527

We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine. ...[more]

PMID: 18941489

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