Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K.
Org Lett. 2016 Nov 18;18(22):5880-5883. doi: 10.1021/acs.orglett.6b02959. Epub 2016 Nov 9.
A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds.
本文报道了一种新的立体选择性无金属顺式二羟基化富电子烯烃的方法，涉及在三氟乙醇（TFE）或六氟异丙醇（HFIP）中与 TEMPO/IBX 反应，并加入合适的亲核试剂。通过正交保护的顺式 1,2-二醇以高非对映选择性控制获得，这些产物可选择性脱保护并选择性官能化，得到具有合成用途的化合物。
