Format

Send to

Choose Destination
Molecules. 2018 Sep 11;23(9). pii: E2317. doi: 10.3390/molecules23092317.

Chiral Diol-Based Organocatalysts in Enantioselective Reactions.

Author information

1
Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building Room 112, Houston, TX 77204-5003, USA. tnnguyen61@uh.edu.
2
Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building Room 112, Houston, TX 77204-5003, USA. pchen25@central.uh.edu.
3
Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom 73000, Thailand. krit_set@silpakorn.edu.
4
Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building Room 112, Houston, TX 77204-5003, USA. jmay@uh.edu.

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.

KEYWORDS:

BINOL; TADDOL; allylation; asymmetric catalysis; conjugate addition; diol catalyst; organoboronates; organocatalysts

PMID:
30208621
DOI:
10.3390/molecules23092317
Free full text

Supplemental Content

Full text links

Icon for Multidisciplinary Digital Publishing Institute (MDPI)
Loading ...
Support Center