Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
Org Lett. 2010 May 7;12(9):2120-2. doi: 10.1021/ol100615j.
An efficient and enantiocontrolled three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters is reported. Enantioenriched alpha-selenyl aldehydes, prepared in one step by asymmetric, organocatalytic alpha-selenylation of aldehydes, were directly subjected to a Wittig reaction followed by allylic selenide to selenoxide oxidation and final spontaneous [2,3]-sigmatropic rearrangement to yield the target compounds in 43-65% overall yield and in 94-97% ee.
报道了一种高效和对映控制的三步合成α-羟基-(E)-β,γ-不饱和酯的方法。通过不对称的、有机催化的醛的α-硒化反应一步制备的手性富集的α-硒基醛，直接进行Wittig 反应，然后进行烯丙基硒醚氧化和最终自发的[2,3]-σ重排，以 43-65%的总收率和 94-97%的ee 值得到目标化合物。
