Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Germany.
J Org Chem. 2010 Aug 20;75(16):5580-9. doi: 10.1021/jo1008959.
Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl(2) to obtain enantiomerically pure alpha-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.
酒石酸盐衍生的硼酸酯 2 可以在 SnCl(2)存在下进行钯催化的羰基烯丙基化反应，得到对映纯的α-取代烯丙基硼酸酯 8 和 9。该反应具有区域选择性和高简单的非对映选择性，形成反式产物。它们与醛的加成反应分别生成对映体富集的同烯丙基醇 17 和 18。本文介绍了它们的合成、表征和机理。
