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Abstract
The chiral norbornene derivatives as one of the C5 main fractions are the important high value-added derivatives of bis(cyclopentadiene), which are derived from cyclopentadiene and asymmetric dienophile via the Diels-Alder reaction. In this paper, based on the mechanism of reaction, the yield and stereoselectivity of the chiral norbornene ester derivatives, aldehydes derivatives, ketone derivatives and acyl oxazolidinone derivatives are reviewed in the presence/absence of catalyst. Generally, the chiral catalysts such as chiral diols, diphenols or oxazolines coordinated with aluminum, boron, copper, titanium or lanthanide metal complexes promote the synthetic rate, stereoselectivity and enantioselectivity of the chiral norbornene derivatives. Meanwhile, the recent applications of chiral norbornene derivatives are briefly reviewed from two aspects: one is the photochromic materials and the other one is the ion exchange membranes, including anion, cation and composite ion exchange membrane. Finally, the future research and applications of the chiral norbornene derivatives are prospected.
Contents
1 Introduction
2 Synthetic mechanism
3 Preparation of chiral norbornene derivatives
3.1 Chiral norbornene ester derivatives
3.2 Chiral norbornene aldehydes derivatives
3.3 Chiral norbornene ketone derivatives
3.4 Chiral norbornene acyl oxazolidinone derivatives
4 Applications of chiral norbornene derivatives
4.1 Optical materials
4.2 Ion exchange membranes
5 Conclusion
Graphical abstract
Keywords
chiral norbornene derivatives
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cyclopentadiene
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dienophile
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Diels-Alder reaction
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Kun Cao, Bei Yuan, Xue Liu, Minfang Wu, Zhen Yao*.
Preparation and Applications of the Chiral Norbornene Derivatives.
Progress in Chemistry, 2017, 29(6): 605-616 DOI:10.7536/PC170127