Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates

doi:10.6023/cjoc202305033

Abstract

Axially chiral compounds are not only important catalysts and ligands in the field of asymmetric synthesis, but also widely exist in many natural products and drugs. Therefore, the development of efficient synthesis of axially chiral compounds has been an important research topic in organic chemistry. Compared with the widely studied vinylidene o-quinone methide (o-VQM) intermediates, the asymmetric catalytic reaction based on the aza-o-VQM intermediates has only attracted people’s attention in recent years, with relatively fewer studies and great potential for development. The progress in the construction of axial chiral compounds through aza-o-VQM intermediates is summarized, and the reaction type, mechanism and synthetic applications are introduced. At last, the prospect of this field is also discussed.

Key words: aza-vinylidene o-quinone methide intermediates, axially chiral compounds, asymmetric catalysis

Cite this article

Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.

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Fig. & Tab. 14

Figure 1. Selected examples of axially chiral natural products, bioactive molecules, ligands and organocatalysts

Scheme 1. Generation of chiral of aza-o-VQMs

Scheme 2. Rational design and possible pathway of the reaction

Scheme 3. Nucleophilic addition of 2-naphthols to aza-o-VQMs intermediates

Scheme 4. Nucleophilic addition of indoles to aza-o-VQMs intermediates

Scheme 5. Synthetic applicability of axially chiral products

Scheme 6. Nucleophilic addition of 4-hydroxycoumarins to aza-o-VQMs intermediates

Scheme 7. Proposed reaction mechanism

Scheme 8. Thiocarbocyclization through aza-o-VQMs intermediates

Scheme 9. Further transformations of axially chiral amino sulfides

Scheme 10. Proposed reaction mechanism

Scheme 11. Heteroannulation through aza-o-VQMs intermediates

Scheme 12. Control experiments and proposed reaction mechanism

Scheme 13. Derivatization of products

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经由氮杂邻联烯醌中间体合成轴手性化合物的研究进展