Add time:08/24/2019         Source:sciencedirect.com

This chapter describes asymmetric reactions employing tartaric acid derivatives as chiral auxiliaries. The ready availability of both enantiomers and existence of four hydroxy groups were conducive to its use for asymmetric synthesis. The following article is basically focused on enantioselective reactions. The first section concerns the characteristics of the carboxylic acid moieties in tartaric acid that were applied to asymmetric reactions. Reactions promoted by tartaric acid itself along with O-protected and acid-protected derivatives are described. In the second section, asymmetric reactions utilizing tartaric acid esters are discussed. The Katsuki-Sharpless epoxidation is one of the main topics as well as various types of reactions mediated by metal salts of tartrate. Next, use of tartramide is discussed. Although chiral auxiliaries without the 2,3-dihydroxybutandioate skeleton are not covered in this chapter, two widely known derivatives, DIOP and TADDOL, that are readily obtained from tartaric acid esters are briefly introduced.

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