Diastereoselective ‘Super Silyl’ Governed Aldol Reaction

In the past few decades modern aldol reactions have been tackling the most common challenges in synthetic chemistry including regio-, chemo-, diastereo- and enantioselectivity. Because all these selectivity challenges can be present in the same reaction, and controlling the outcome of such a process has become of imminent need, especially in the assembly of complex polyoxygenated natural products. In this context, the group of Professor Hisashi Yamamoto at the Chubu University (Japan) wanted to make a contribution towards solving these selectivity issues for the synthesis of complex polyols. In continuation of their previous work on the Lewis acid catalyzed Mukaiyama aldol reaction of super silyl enol ethers, they put their focus on the construction of α,β-dioxygenated aldehydes.

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