Department of Inorganic and Organic Chemistry, Section of Inorganic Chemistry and Institut de Química Teòrica i Computacional de la Universitat de Barcelona, Universitat de Barcelona, Carrer Martí i Franqués 1-11, 08028 Barcelona, Spain.
X-Ray Diffraction Unity, CCiTUB, Universitat de Barcelona, Carrer Solé i Sabarís 1-3, 08028 Barcelona, Spain.
Org Lett. 2023 Feb 3;25(4):659-664. doi: 10.1021/acs.orglett.2c04254. Epub 2023 Jan 26.
A direct and asymmetric -aldol reaction of -acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon-carbon bond-forming reactions, can be smoothly removed to give access to a variety of enantiomerically pure compounds with high synthetic value.
在[DTBM-SEGPHOS]NiCl、TMSOTf 和 lutidine 的存在下，通过芳基缩醛与二烷基缩醛的直接不对称 -aldol 反应，从 - 酰基 -1,3-噁嗪烷-2-硫酮合成了多种具有高合成价值的对映纯化合物。已确定首次用作不对称碳-碳键形成反应骨架的噁嗪烷硫酮杂环可以被顺利去除。
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