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Synthesis 2021; 53(07): 1229-1236
DOI: 10.1055/a-1325-4092
short review

Catalytic Asymmetric Osmium-Free Dihydroxylation of Alkenes

Shixia Su
a   Hefei National Laboratory for Physical Science at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
,
Chuan Wang  ∗
a   Hefei National Laboratory for Physical Science at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
b   Center for Excellence in Molecular Synthesis of CAS, Hefei, Anhui 230026, P. R. of China
› Author AffiliationsThis work is supported by National Natural Science Foundation of China (Grant No. 21772183, 22071230), Fundamental Research Funds for the Central Universities (WK2060190086), ‘1000-Youth Talents Plan’ start-up funding, as well as University of Science and Technology of China.
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Abstract

Asymmetric dihydroxylation of alkenes is one of the cornerstone reactions in organic synthesis, providing a direct entry to optically active vicinal diols, which are not only a subunit in natural products but also versatile building blocks. In recent years, considerable progress in catalytic asymmetric osmium-free dihydroxylation has been achieved. This short review presents a concise summary of the reported methods of catalytic asymmetric osmium-free dihydroxylation.

1 Introduction

2 Iron-Catalyzed Asymmetric syn-Dihydroxylation of Alkenes

3 Manganese-Catalyzed Asymmetric syn-Dihydroxylation of Alkenes

4 Palladium/Gold Bimetallic Nanocluster-Catalyzed Asymmetric syn-Dihydroxylation of Alkenes

5 Enzyme-Catalyzed Asymmetric anti-Dihydroxylation of Alkenes

6 Amine-Catalyzed Asymmetric Formal anti-Dihydroxylation of Enals

7 Diselenide-Catalyzed anti-Dihydroxylation of Alkenes

8 Molybdenum-Catalyzed Asymmetric anti-Dihydroxylation of Allylic­ Alcohols

9 Phase-Transfer-Catalyzed Asymmetric Dihydroxylation of α-Aryl Acrylates

10 Conclusion

Key words

dihydroxylation - vicinal diol - oxidation - alkene - asymmetric catalysis


Publication History

Received: 27 October 2020

Accepted after revision: 30 November 2020

Accepted Manuscript online:
30 November 2020

Article published online:
29 January 2021

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