Rhodium-Catalyzed N-Allylation of Thymine

P. A. Evans; K. W. Lai; H.-R. Zhang; J. C. Huffman

doi:10.1055/s-2006-934501

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Synfacts 2006(6): 0560-0560
DOI: 10.1055/s-2006-934501

Synthesis of Heterocycles

Rhodium-Catalyzed N-Allylation of Thymine

Contributor(s): Victor Snieckus, Yigang Zhao
P. A. Evans*, K. W. Lai, H.-R. Zhang, J. C. Huffman
Indiana University, Bloomington, USA

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Publication History

Publication Date:
19 May 2006 (online)

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Significance

Regioselective and enantiospecific Rh-catalyzed allylic substitutions of N³-benzoylthymine are reported. The Rh-catalyzed reactions with racemic allylic carbonates 1 give predominantly more highly substituted allylic products with or without debenzoylation as a function of temperature. When chiral carbonates 2 are used, the reactions proceed regioselectively but also with enantiospecificity. One of the products was converted into the new, conformationally rigid nucleoside 3 using a stereoselective free radical cyclization strategy.