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CC BY-NC-ND 4.0 · SynOpen 2021; 05(01): 68-85
DOI: 10.1055/s-0040-1706028
review

Atropisomerism in Styrene: Synthesis, Stability, and Applications

Jia Feng
a   Department of Chemistry and Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China
,
Zhenhua Gu  ∗
a   Department of Chemistry and Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. of China
b   Ocean College, Minjiang University, Fuzhou, Fujian 350108, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (21901236, 21871241).
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Abstract

Atropisomeric styrenes are a class of optically active compounds, the chirality of which results from restricted rotation of the C(vinyl)–C(aryl) single bond. In comparison with biaryl atropisomers, the less rigid skeleton of styrenes usually leads them to have lower rotational barriers. Although it has been overlooked for a long time, scientists have paid attention to this class of unique molecules in recent years and have developed many methods for the preparation of optically active atropisomeric styrenes. In this article, we review the development of the concept of atropisomeric styrenes, along with their isolation, asymmetric synthesis, and synthetic applications.

1 Introduction

2 The Concept of Styrene Atropisomerism

3 Early Research: Separation of Optically Active Styrenes

4 Synthesis of Optically Active Styrenes

5 Stability of the Chirality of Atropisomeric Styrenes

6 Outlook

Key words

atropisomers - styrene - axial chirality - asymmetric synthesis - asymmetric C–H functionalization


Publication History

Received: 25 January 2021

Accepted after revision: 02 February 2021

Article published online:
10 March 2021

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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