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Synthesis 2024; 56(08): 1259-1272
DOI: 10.1055/a-2159-1688
DOI: 10.1055/a-2159-1688
short review
Progress on the Enantioselective Synthesis of Axially Chiral Cycloalkylidenes
We gratefully acknowledge funding in support of this work from the National Natural Science Foundation of China (21871240), the State Key Laboratory of Elemento-organic Chemistry, Nankai University (202001), the Fundamental Research Funds for the Central Universities (WK2060000017), and the Open Project of Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University (KFJJ2022013).
Abstract
The discovery of new asymmetric synthetic methodologies and the asymmetric synthesis of new chiral compounds have been a major focus of synthetic organic chemists for decades. Axially chiral compounds have gained considerable attention in recent years because of their widespread utility in asymmetric catalysis and synthesis. Methods for the asymmetric synthesis of axially chiral cycloalkylidenes, a subset of axially chiral molecules, are far fewer compared to those developed for the preparation of chiral allenes and chiral biaryl compounds. In this review, different approaches for the synthesis of axially chiral cycloalkylidenes are summarized.
1 Introduction
2 Methods for the Enantioselective Synthesis of Axially Chiral Cycloalkylidenes
2.1 Asymmetric Synthesis of Axially Chiral Cycloalkylidenes
2.1.1 Asymmetric Horner–Wadsworth–Emmons (HWE) Reactions
2.1.2 Asymmetric Wittig Reactions
2.1.3 Asymmetric Dehydrohalogenation Reactions
2.1.4 Asymmetric Elimination Reactions of Chiral Sulfoxides/Selenoxides
2.1.5 Kinetic Resolution of Prochiral Compounds
2.1.6 Other Miscellaneous Methods
2.2 Catalytic Asymmetric Synthesis of Axially Chiral Cycloalkylidenes
3 Conclusion
Key words
chiral cycloalkylidenes - asymmetric synthesis - asymmetric Wittig-type reaction - chiral auxiliary - kinetic resolution - chiral cyclohexadienoximePublication History
Received: 24 July 2023
Accepted after revision: 23 August 2023
Accepted Manuscript online:
23 August 2023
Article published online:
17 October 2023
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