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Synthesis 2021; 53(24): 4588-4598
DOI: 10.1055/a-1577-7850
short review

Development of Synthetic Strategies to Access Optically Pure ­Feringa’s Motors

Yu-Nan Qin‡
a   Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry & Chemical Engineering, Hubei University, Wuhan 430062, P. R. of China
,
Chen Zhang‡
a   Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry & Chemical Engineering, Hubei University, Wuhan 430062, P. R. of China
,
Quan Li  ∗
a   Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry & Chemical Engineering, Hubei University, Wuhan 430062, P. R. of China
,
Guang-Yan Du∗
b   College of Materials Science and Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
› Author AffiliationsSupport for this research was provided by the National Natural Science Foundation of China (21901067), from the Ministry of Human Resources and Social Security of China (Starting Grant to Q.L.), and Zhejiang Provincial Natural Science Foundation of China (LY19B040005) (Grant to G.Y.D.).
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Abstract

Light-driven unidirectional molecular motors have gained significant attention since the pioneering work by Prof. Ben Feringa in 1999, and they hold great promise as next-generation smart materials. The intrinsic feature of point chirality and the helicity of these molecular motors requires efficient strategies to access their optically pure forms, especially when chirality-sensitive materials are fabricated. In this short review, we summarize synthetic strategies to access optically pure first- and second-generation molecular motors. Three general strategies are discussed: direct asymmetric synthesis, chiral auxiliary methods and chiral separation aided by a resolving agent. We hope that this review will ignite the enthusiasm of synthetic chemists to address very fundamental but unavoidable synthetic questions on chiral-alkene-based molecular motors concerning their large-scale appli­cations.

1 Introduction

2 Synthesis of First-Generation Molecular Motors

2.1 Direct Asymmetric Synthesis of Molecular Motors

2.2 Resolving-Agent-Aided Chiral Resolution of Molecular Motors

3 Synthesis of Second-Generation Molecular Motors

3.1 Direct Asymmetric Synthesis of Molecular Motors

3.2 Chiral Auxiliary Strategy

3.3 Domino Strategy

4 onclusions

Key words

molecular machines - molecular motors - overcrowded alkenes - McMurry reaction - Barton–Kellogg reaction - enantioselectivity


Publication History

Received: 28 June 2021

Accepted after revision: 03 August 2021

Accepted Manuscript online:
03 August 2021

Article published online:
22 September 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
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