Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006, Madrid, Spain.
Chemistry. 2020 Apr 6;26(20):4620-4632. doi: 10.1002/chem.201905742. Epub 2020 Mar 18.
The chemo- and stereocontrolled functionalization of conjugated sulfinyl dienes in a cascade process that involves a conjugate addition, diastereoselective protonation and a [2,3]-sigmatropic rearrangement is reported. Enantioenriched 1,4-diol and 1,4-aminoalcohol derivatives are obtained in a very straightforward manner. Further functionalization of these structures, including highly stereoselective epoxidation, dihydroxylation and the stereodivergent synthesis of several polyols in a controlled fashion is described.
本文报道了一种通过串联反应，即共轭加成、立体选择性质子化和[2,3]-σ迁移重排，对共轭亚磺酰二烯进行化学和立体控制官能化的方法。以非常直接的方式获得了对映体富集的 1,4-二醇和 1,4-氨基醇衍生物。进一步对这些结构进行官能化，包括高度立体选择性的环氧化、双羟化以及以可控方式合成几种多元醇的立体发散合成。
