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Issue 21, 2018
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Enantioselective and regiodivergent allylation of pyrimidines with terminal allenes: an approach to pyrimidine acyclic nucleosides

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Abstract

An atom-economic addition of pyrimidines to allenes has been developed for the diverse synthesis of branched or linear N-allylpyrimidine analogues. With [Rh(COD)Cl]2/chiral MeOBIPHEP as the catalyst, the asymmetric allylation reaction proceeded well and afforded the branch selective adducts in good yields, with high regio- and enantioselectivities. Meanwhile, when [Pd(η3-allyl)Cl]2/DPPF was used as the catalyst, the linear-selective allylation of pyrimidines could be carried out in good yields. Here, the configuration of the C[double bond, length as m-dash]C bond in the side chain of the products was mainly found to be the E-form.

Graphical abstract: Enantioselective and regiodivergent allylation of pyrimidines with terminal allenes: an approach to pyrimidine acyclic nucleosides

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Publication details

The article was received on 06 Aug 2018, accepted on 26 Sep 2018 and first published on 26 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00827B
Citation: Org. Chem. Front., 2018,5, 3148-3152
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    Enantioselective and regiodivergent allylation of pyrimidines with terminal allenes: an approach to pyrimidine acyclic nucleosides

    L. Liang, H. Niu, M. Xie, G. Qu and H. Guo, Org. Chem. Front., 2018, 5, 3148
    DOI: 10.1039/C8QO00827B

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