Elsevier

Tetrahedron Letters

Volume 43, Issue 30, 22 July 2002, Pages 5297-5300
Tetrahedron Letters

Tandem reactions initiated by the oxidative decarboxylation of 1-benzoyl-2(S)-tert-butyl-6(S)-carboxyperhydropyrimidin-4-one

https://doi.org/10.1016/S0040-4039(02)01066-3Get rights and content

Abstract

Treatment of the title perhydropyrimidinone with diacetoxyiodobenzene and iodine followed by addition of allyltrimethylsilane and boron trifluoride etherate afforded 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(H)-pyrimidin-4-one in 65–71% yield, via an efficient three-step radical decarboxylation-oxidation-β-elimination tandem reaction. In contrast, when addition of allyltrimethylsilane/BF3·OEt2 was suppressed, a remarkable five-step tandem process led to the formation of vinylic iodide, 1-benzoyl-2(S)-tert-butyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one as the main product.

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Acknowledgements

We are indebted to CONACyT, Mexico, for financial support via grant 33023-E and the Cátedra Patrimonial de Excelencia granted to M.A.I.A.

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