Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Org Biomol Chem. 2020 Feb 14;18(6):1204-1213. doi: 10.1039/c9ob02472g. Epub 2020 Jan 29.
The synthesis of α-aryl- and α-alkyl-substituted serine derivatives via [3,3]-sigmatropic rearrangement of allyl carbamates as a key step is reported. Allyl carbamates were obtained from the corresponding allyl alcohols. The former were prepared through three approaches. Aryl-substituted ones were synthesized via the Stille coupling reaction of aryl iodides with enantiomerically enriched vinyl stannanes. Conversely, alkyl-substituted allyl alcohols were prepared by an analogous strategy involving the Negishi coupling reaction of enantiomerically enriched vinyl iodides or by enzymatic kineric resolution of the corresponding racemic alcohols.
本文报道了通过[3,3]-σ重排反应合成α-芳基和α-烷基取代丝氨酸衍生物的方法，其中烯丙基氨基甲酸酯作为关键步骤。烯丙基氨基甲酸酯由相应的烯丙基醇制备。前者通过三种方法制备。芳基取代物通过芳基碘与对映体富集的乙烯基锡烷的 Stille 偶联反应合成。相反，烷基取代的烯丙基醇通过类似的策略制备，包括对映体富集的乙烯基碘的 Negishi 偶联反应或通过相应外消旋醇的酶动力学拆分。
