Next Article in Journal
Amino Acids in the Development of Prodrugs
Previous Article in Journal
Hexanoic, Octanoic and Decanoic Acids Promote Basal and Insulin-Induced Phosphorylation of the Akt-mTOR Axis and a Balanced Lipid Metabolism in the HepG2 Hepatoma Cell Line
Previous Article in Special Issue
Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts
Article Menu
Issue 9 (September) cover image

Export Article

Open AccessReview
Molecules 2018, 23(9), 2317;

Chiral Diol-Based Organocatalysts in Enantioselective Reactions

Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building Room 112, Houston, TX 77204-5003, USA
Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom 73000, Thailand
Author to whom correspondence should be addressed.
Received: 21 August 2018 / Revised: 3 September 2018 / Accepted: 6 September 2018 / Published: 11 September 2018
(This article belongs to the Collection Recent Advances in Organocatalysis)


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. View Full-Text
Keywords: asymmetric catalysis; organocatalysts; organoboronates; allylation; conjugate addition; BINOL; TADDOL; diol catalyst asymmetric catalysis; organocatalysts; organoboronates; allylation; conjugate addition; BINOL; TADDOL; diol catalyst

Scheme 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Share & Cite This Article

MDPI and ACS Style

Nguyen, T.N.; Chen, P.-A.; Setthakarn, K.; May, J.A. Chiral Diol-Based Organocatalysts in Enantioselective Reactions. Molecules 2018, 23, 2317.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top