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• Review •

Oxidative Kinetic Resolution of Secondary Alcohols

Zhang Yuecheng, Zhao Shanshan, Mi Guorui, Zhao Jiquan*   

  1. School of Chemical Engineering, Hebei University of Technology, Tianjin 300130, China
  • Received: Revised: Online: Published:
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Optically active alcohols are extremely important starting materials and key intermediates for the synthesis of pharmaceutically and biologically active compounds. They can be obtained by oxidative kinetic resolution of racemic alcohols. In this review the recent progress in the oxidative kinetic resolution of secondary alcohols is discussed according to the kind of the oxidants and chiral catalysts. In addition, the mechanisms of some methods for the resolution of secondary alcohols are also discussed. The oxidative kinetic resolution of secondary alcohols using (-)-sparteine-Pd(Ⅱ), sparteine analogues-Pd(Ⅱ), N-heterocyclic carbine(NHC)-Pd(Ⅱ), chiral difunctional-Ir complexes and chiral (ON)-Ru(salen) complexes as catalyst systems respectively, and molecular oxygen as terminal oxidant are fully discussed. Besides, the resolution of secondary alcohols with chiral salen-Mn(Ⅲ) complex as catalyst and (diacetoxyiodo)benzene as terminal oxidant, and by the means of asymmetric transfer hydrogenation are also discussed. It is found that (-)-sparteine-Pd(Ⅱ)-O2 is the best among all the systems employed in the oxidative kinetic resolution of secondary alcohols. The novel system with high performance in the oxidative kinetic resolution of secondary alcohols need to be developed. Contents
1 Introduction
2 Using molecular oxygen as oxidant
2.1 Sparteine-Pd(Ⅱ) catalyst system
2.2 Sparteine analogues-Pd(Ⅱ) catalyst system
2.3 N-heterocyclic carbine(NHC)-Pd catalyst system
2.4 Chiral difunctional-Ir catalyst system
2.5 Chiral (ON)-Ru(salen) complex catalyst system
3 Salen-Mn(Ⅲ)-(diacetoxyiodo)benzene system
4 Resolution of secondary alcohols by asymmetric transfer hydrogenation
5 Conclusion
Key words: oxidative kinetic resolution, secondary alcohols, chiral catalysts

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