A Chiral Building Block for the ­Stereocontrolled Installation of the 1,3‐Diol Motif (Eur. J. Org. Chem. 2/2016)

Abstract

The cover picture shows a newly developed building block, which gives a simple and flexible access to 1,3‐diols as demonstrated in the Communication by S. F. Kirsch et al. on p. . This building block is chiral, and the stereogenic center that is part of the building block is unambiguously fixed. Attaching the building block to an aldehyde through olefination followed by substrate‐directed reduction then allows for the stereocontrolled creation of a 1,3‐diol unit. For example, both diastereomers of the naturally occurring 1,2,4‐trihydroxynonadecane, isolated from the unripe avocado fruit, can be synthesized in a stereocontrolled way by using this building block: One compound to create them all ...