Laboratory of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan.
Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka, 569-1094, Japan.
Chemistry. 2018 Dec 12;24(70):18638-18642. doi: 10.1002/chem.201804794. Epub 2018 Nov 26.
Iodocyclization of silyl group-substituted homopropargylic carbamates and amides proceeded via 6-exo-dig mode to afford 6-vinylene-4,5-dihydro-1,3-oxazines in moderate to quantitative yields. This is the first report for silyl group-solely directed iodocyclization of alkynes utilizing the β-silyl effect. Under these mild reaction conditions, various functionalities such as secondary alcohol, acetal, urea, and sulfide were tolerated.
硅基取代的偕丙氨酸酯和酰胺的碘环化反应通过 6-endo-dig 模式进行，以中等至定量的收率得到 6-乙烯基-4,5-二氢-1,3-恶嗪。这是首例利用β-硅基效应仅由硅基导向的炔烃的碘环化反应。在这些温和的反应条件下，各种官能团如仲醇、缩醛、脲和硫化物都可以耐受。
