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

✍ Scribed by Martı́n A. Iglesias-Arteaga; C.Gabriela Avila-Ortiz; Eusebio Juaristi

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 175 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01066-3

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✦ Synopsis

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-b-elimination tandem reaction. In contrast, when addition of allyltrimethylsilane/BF 3 •OEt 2 was suppressed, a remarkable five-step tandem process led to the formation of vinylic iodide, 1-benzoyl-2(S)-tertbutyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one as the main product.

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