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Abstract
Among the challenges facing asymmetric synthesis the selective construction of quaternary stereogenic centres, particularly those bearing all-carbon substituents, stands out. The aldol reaction has the potential to create such stereocentres, but, despite the many advances in this field, a highly selective and efficient procedure has remained elusive. Here we show that, by choosing an alternative retrosynthetic approach, such products can be prepared in a highly selective fashion. Through the consecutive addition of several organometallic derivatives, an allylzinc reagent is prepared and, on addition to an aldehyde, an aldol-type product is created. The one-pot operation involves the construction of three new carbon–carbon bonds and the formation of an all-carbon quaternary stereocentre. The products of the reaction are amenable to downstream modification, and the procedure should find applications in the fields of natural product synthesis and drug discovery. The enantioselective construction of quaternary stereocentres, particularly those with all-carbon substituents, is a challenging problem in asymmetric synthesis. It has now been shown that an alternative retrosynthesis of aldol products provides an opportunity to form such stereocentres with a reaction that creates three new carbon–carbon bonds in a single step. Cite this article
Das, J., Chechik, H. & Marek, I. A unique approach to aldol products for the creation of all-carbon quaternary stereocentres. Nature Chem 1, 128–132 (2009). https://doi.org/10.1038/nchem.131 