Recent advances in the diastereoselective Reformatsky-type reaction.

The classical Reformatsky reaction introduced for the first time in 1887 has been recognized as one among the most useful methods for C-C bond formation. Diastereoselective versions based on the use of chiral auxiliaries as well as enantioselective protocols using chiral ligands have been successfully developed during the last few years. This tutorial review highlights the main recent achievements (since 2004) in the diastereoselective Reformatsky reaction; diastereochemical control has been efficiently achieved using a large variety of chiral auxiliaries to perform the synthesis of specific cyclic and acyclic chiral moieties. The diastereoselective Reformatsky reactions employed in the total synthesis of natural products are also described.

Efficient and stereoselective access to the polyol fragment C9-C16 of ansamycin antibiotics.

Efficient synthesis of the fragment C9-C16 bearing the anti,syn stereotriad of ansamycin antibiotics is described. Key steps for controlling the configuration of the three stereogenic centers involve a stereoselective Reformatsky-type reaction followed by a diastereoselective reduction of a beta-ketosulfoxide.