Structures and Synthetic Strategies of Chiral Oxazolinyl Ferrocene Derivatives

doi:10.6023/cjoc202201037

Abstract

In the past two decades, chiral oxazolinyl ferrocenes and their corresponding transition-metal complexes have been investigated as one of the most significant catalysts in asymmetric transformations. The synthesis of oxazolinyl ferrocenes established the key structural foundation for achieving the chiral catalysts with excellent activity and stereoselective control. In this review, the typical derivatives with oxazolinyl ferrocenes framework are surveyed, and the practical preparation strategies for chiral oxazolinyl ferrocenes in recent years are overviewed. The potential challenges and further applications in the field of oxazolinyl ferrocene derivatives are also delivered.

Key words: oxazoline, ferrocene, chiral ligands, ring-closure reaction

Cite this article

Li Dai, Di Xu, Yifei Mao, Jiaqi Zhu, Mengjiao Yang. Structures and Synthetic Strategies of Chiral Oxazolinyl Ferrocene Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2364-2375.

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Fig. & Tab. 28

Figure 1. Biologically active compounds with ferrocene moiety

Figure 2. Examples of typical chiral ligands with oxazoline fragments

Figure 3. Typical planar chiral oxazolinyl ferrocene ligands and catalysts

Scheme 1. Mechanism of ortho-lithiation process of chiral oxazolinyl ferrocene

Figure 4. 1,1'-Disubstituted oxazolinyl ferrocene compounds

Figure 5. Oxazolinyl bisphosphine ferrocene compounds

Figure 6. C2-Symmetric bisoxazolinyl ferrocenes

Figure 7. Tetrasubstituted bisoxazolinyl ferrocene compounds

Figure 8. Monosubstituted oxazolinyl ferrocene compounds

Scheme 2. Synthesis of oxazoline through ring-closure reaction of thionyl chloride

Scheme 3. Synthesis of oxazoline through ring-closure reaction by Appel reaction

Scheme 4. Synthesis of oxazoline through ring-closure reaction of methane sulfonyl chloride

Scheme 5. Synthesis of oxazoline through ring-closure reaction of p-toluenesulfonyl chloride

Scheme 6. DMAP catalyzed synthesis of oxazoline

Scheme 7. Synthesis of 4-hydroxymethyl oxazoline through ring-closure reaction

Scheme 8. Synthesis of oxazoline through ring-closure reaction of Vilsmeier reagent

Scheme 9. Synthesis of 4-carboxylic ester oxazolinyl ferrocene via Appel reaction

Scheme 10. Synthesis of 4-carboxylic ester oxazolinyl ferrocene by DAST reagent

Scheme 11. Synthesis of 4-carboxylic ester oxazolinyl ferrocene by Burgess reagent

Scheme 12. Synthesis of oxazoline through ring-closure reaction from imidates

Scheme 13. Synthesis of oxazoline through ring expansion of N-ferrocenoyl-aziridine-2-carboxylic esters

Scheme 14. Synthesis of oxazolinyl ferrocenes from cyano ferrocene and β-amino alcohols

Scheme 15. Synthesis of oxazolinyl ferrocene from ferrocene carboxylic esters catalyzed by samarium trichloride

Scheme 16. Synthetic method of 1'-substituted oxazolinyl ferrocenes

Scheme 17. Synthetic method of 1'-diphenylphosphine oxazolinyl ferrocenes

Scheme 18. Synthetic method of 1'-silyl ether substituted oxazolinyl ferrocene

Scheme 19. Synthesis of oxazoline through ring-closure reaction based on planar chiral ferrocenyl substrates

Scheme 20. Synthesis of planar chiral oxazolinyl ferrocene ligands from Ugi amine

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