手性噁唑啉二茂铁化合物结构与合成方法

doi:10.6023/cjoc202201037

摘要/Abstract

手性噁唑啉二茂铁及相应过渡金属络合物是近二十年来不对称合成反应中标志性的催化剂之一, 噁唑啉二茂铁合成是获得这类高活性及立体选择性催化剂的重要结构基础. 梳理了以噁唑啉二茂铁为基本结构的典型衍生物种类, 综述了近期多种噁唑啉二茂铁的实用合成方法, 同时指出开发新型噁唑啉二茂铁化合物面临的挑战和发展方向.

关键词: 噁唑啉, 二茂铁, 手性配体, 成环反应

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

引用此文

戴力, 徐迪, 毛翼斐, 朱嘉琦, 杨梦娇. 手性噁唑啉二茂铁化合物结构与合成方法[J]. 有机化学, 2022, 42(8): 2364-2375.

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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图/表 28

图1. 含二茂铁片段的生物活性化合物

Figure 1. Biologically active compounds with ferrocene moiety

图2. 典型含噁唑啉片段手性配体举例

Figure 2. Examples of typical chiral ligands with oxazoline fragments

图3. 典型平面手性噁唑啉二茂铁配体/催化剂结构

Figure 3. Typical planar chiral oxazolinyl ferrocene ligands and catalysts

图式1. 手性噁唑啉二茂铁邻位锂化过程机理

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

图4. 1,1'-双取代噁唑啉二茂铁化合物

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

图5. 噁唑啉-双膦二茂铁化合物

Figure 5. Oxazolinyl bisphosphine ferrocene compounds

图6. C2-对称双噁唑啉二茂铁化合物

Figure 6. C2-Symmetric bisoxazolinyl ferrocenes

图7. 四取代双噁唑啉二茂铁化合物

Figure 7. Tetrasubstituted bisoxazolinyl ferrocene compounds

图8. 单取代噁唑啉二茂铁化合物

Figure 8. Monosubstituted oxazolinyl ferrocene compounds

图式2. 二氯亚砜条件下噁唑啉成环反应

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

图式3. 利用Appel反应噁唑啉成环反应

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

图式4. 甲烷磺酰氯条件下噁唑啉成环反应

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

图式5. 对甲苯磺酰氯条件下噁唑啉成环反应

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

图式6. DMAP催化条件下噁唑啉合成

Scheme 6. DMAP catalyzed synthesis of oxazoline

图式7. 4-羟基甲基噁唑啉二茂铁的合成

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

图式8. Vilsmeier试剂条件下噁唑啉成环反应

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

图式9. 利用Appel反应4-羧酸甲酯噁唑啉二茂铁的合成

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

图式10. DAST试剂合成4-羧酸酯噁唑啉二茂铁

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

图式11. Burgess试剂合成4-羧酸酯噁唑啉二茂铁

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

图式12. 以亚氨酸酯为底物噁唑啉成环反应

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

图式13. 以N杂环丙烷2-羧酸酯为底物开环反应合成噁唑啉环

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

图式14. 氰基二茂铁与β-氨基醇的噁唑啉二茂铁合成

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

图式15. 以二茂铁甲酸酯为底物三氯化钐催化合成噁唑啉二茂铁

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

图式16. 1'-取代噁唑啉二茂铁合成方法

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

图式17. 1'-二苯基膦噁唑啉二茂铁合成方法

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

图式18. 1'-硅醚基团取代噁唑啉二茂铁合成方法

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

图式19. 基于平面手性二茂铁底物的噁唑啉成环反应

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

图式20. 以Ugi胺为原料平面手性噁唑啉二茂铁配体合成

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

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