Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (6): 2267-2274.DOI: 10.6023/cjoc202512024 Previous Articles     Next Articles

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手性香料(–)-薄荷醇的不对称合成进展

刘如灿a, 唐杰a, 朱立军a, 马明a,*(), 胡旭东b,*(), 刘文博b   

  1. a 烟叶资源科学利用重庆市重点实验室 重庆 400060
    b 武汉大学化学与分子科学学院 武汉 430072
  • 收稿日期:2025-12-18 修回日期:2026-01-25 发布日期:2026-03-20
  • 基金资助:
    重庆中烟工业有限责任公司科技(HX20230204)

Advances in the Asymmetric Synthesis of Chiral Fragrance (–)-Menthol

Rucan Liua, Jie Tanga, Lijun Zhua, Ming Maa,*(), Xudong Hub,*(), Wenbo Liub   

  1. a Chongqing Key Laboratory of Scientific Utilization of Tobacco Resources, Chongqing 400060
    b College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
  • Received:2025-12-18 Revised:2026-01-25 Published:2026-03-20
  • Contact: * E-mail: gracemaming5418@163.com;ylhuxd@whu.edu.cn
  • Supported by:
    Science and Technology Project of China Tobacco Chongqing Industrial Company Limited(HX20230204)

The unique flavor of (–)-menthol makes it widely used in the fields of food, medicine, and daily chemicals. The continuously growing market demand has driven the rapid development of efficient asymmetric synthetic routes. This review summarizes the mainstream industrial synthesis routes and advances in asymmetric catalysis of (–)-menthol, aiming to outline the development and technological evolution of its synthetic strategies. Currently, three major technical pathways are predominantly employed in industrial production: the Symrise route obtains the target product via chiral resolution; the Takasago process achieves highly selective synthesis of key intermediates through rhodium-catalyzed asymmetric isome- rization. While the BASF route directly affords the crucial intermediate citronellal via rhodium-catalyzed asymmetric hydrogenation of citral. Furthermore, synthetic diversity is also provided by reductive strategies using piperitenone as a precursor and transfer hydrogenation approaches catalyzed by organocatalysts. Notably, the recent design of a chiral strong Brønsted acid catalyst by the List group, which enables highly selective cyclization of neral through a spatial confinement effect. This advancement offers a valuable paradigm for developing novel synthetic processes with enhanced step and atom economy.

Key words: (–)-menthol, asymmetric synthesis, chiral fragrances