Chiral Diol-Based Organocatalysts in Enantioselective Reactions

Organocatalysis has emerged as a powerful synthetic tool in organic chemistry in the last few decades. Among various classes of organocatalysis, chiral diol-based scaffolds, such as BINOLs, VANOLs, and tartaric acid derivatives, have been widely used to induce enantioselectivity due to the ability of the hydroxyls to coordinate with the Lewis acidic sites of reagents or substrates and create a chiral environment for the transformation. In this review, we will discuss the applications of these diol-based catalysts in different types of reactions, including the scopes of reactions and the modes of catalyst activation. In general, the axially chiral aryl diol BINOL and VANOL derivatives serve as the most competent catalyst for most examples, but examples of exclusive success using other scaffolds, herein, suggests that they should not be overlooked. Lastly, the examples, to date, are mainly from tartrate and biaryl diol catalysts, suggesting that innovation may be available from new diol scaffolds.

Resolution of P-stereogenic P-heterocycles via the formation of diastereomeric molecular and coordination complexes (a review)

TADDOL derivatives and the Ca2+-salts of tartaric acid derivatives were found to be versatile and generally applicable resolving agents for the preparation of the enantiomers of P-stereogenic heterocyclic phosphine oxides and phosphinates.

Chiral liquid membrane for enantioselective separation of racemic ibuprofen by l-tartaric acid derivatives

Use of a chiral liquid membrane is an attractive separation method for racemic ibuprofen, and the separation factor could be up to 1.38 under optimal experimental conditions.