Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
J Am Chem Soc. 2010 Apr 21;132(15):5354-6. doi: 10.1021/ja101076q.
In this communication, we report that substrate-controlled 1,5-syn and -anti stereoinduction in the aldol reaction of beta-tris(trialkylsilyl)siloxy methyl ketones can be achieved with high diastereoselectivities. Tris(trialkylsilyl)silyl groups are easily prepared and play an important role in the selectivities of these reactions. Furthermore, all of the 1,3,5-triol stereoisomers can easily be prepared from beta-siloxy methyl ketones in no more than three steps.
在本通讯中,我们报道了β-三(三烷基硅基)硅氧基甲基酮的醛醇反应中,可以通过高非对映选择性实现底物控制的 1,5-顺式和反式立体诱导。三(三烷基硅基)硅基基团易于制备,并在这些反应的选择性中起着重要作用。此外,所有的 1,3,5-三醇立体异构体都可以很容易地通过β-硅氧基甲基酮在不超过三步的反应中制备得到。