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Synthesis 2021; 53(23): 4341-4352
DOI: 10.1055/a-1533-3085
short review

Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Xinhui Yu‡
a   Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong, 250012, P. R. of China
,
Ting Zhang‡
a   Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong, 250012, P. R. of China
,
Jitian Liu∗
a   Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong, 250012, P. R. of China
,
Xiaoxun Li∗
a   Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong, 250012, P. R. of China
b   Suzhou Institute of Shandong University, NO.388 Ruoshui Road, SIP, Suzhou, Jiangsu, 215123, P. R. of China
› Author AffiliationsThe research was funded by the National Natural Science Foundation of China (21901142), the Natural Science Foundation of Shandong Province (ZR2019QB001, ZR2020QB017), the Natural Science Foundation of Jiangsu Province (BK20180227), and the Fundamental Research Fund of Shandong University (21310082164009, 21310088963023, 2020QNQT007, 2020QNQT009).
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Abstract

Palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) provides an efficient and powerful strategy to construct quaternary stereocenters, which are widely present in biologically active natural products and approved drugs. In this short review, we summarize recent developments (since 2018) in the facile synthesis of quaternary stereocenters via DAAA methods. Several representative examples of the use of DAAA strategies for the total synthesis of complex natural products further demonstrate its synthetic potential in the realm of organic and medicinal chemistry.

1 Introduction

2 Construction of Quaternary Stereocenters via Palladium Catalyzed DAAA

3 Construction of Quaternary Stereocenters via Pd-Catalyzed Interceptive DAAA

4 Application of DAAA in Natural Product Synthesis

5 Conclusion

Key words

quaternary stereocenters - decarboxylative allylic alkylation - asymmetric catalysis - palladium - synthetic application


Publication History

Received: 22 May 2021

Accepted after revision: 22 June 2021

Accepted Manuscript online:
22 June 2021

Article published online:
22 July 2021

© 2021. Thieme. All rights reserved

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