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Molecules 2018, 23(9), 2317; https://doi.org/10.3390/molecules23092317

Chiral Diol-Based Organocatalysts in Enantioselective Reactions

1
Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building Room 112, Houston, TX 77204-5003, USA
2
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)

Abstract

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

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