Alamillo-Ferrer Carla, Davidson Stuart C, Rawling Michael J, Theodoulou Natalie H, Campbell Matthew, Humphreys Philip G, Kennedy Alan R, Tomkinson Nicholas C O
WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
GlaxoSmithKline Medicines Research Centre , Gunnels Wood Road, Stevenage SG1 2NY, United Kingdom.
Org Lett. 2015 Oct 16;17(20):5132-5. doi: 10.1021/acs.orglett.5b02674. Epub 2015 Oct 1.
Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.
由市售二酸一步制备的丙二酰过氧化物1是用于烯烃反式二羟基化的有效试剂。1与烯烃在乙酸存在下于40℃反应，随后进行碱性水解，得到相应的二醇（产率35 - 92%），反式选择性高达13:1。提出了一种与实验结果一致的机理解释所观察到的选择性。
