手性降冰片烯衍生物的制备及应用

曹堃; 袁贝; 刘学; 吴敏芳; 姚臻*

doi:10.7536/PC170127

化学进展 ›› 2017, Vol. 29 ›› Issue (6) :605-616 DOI: 10.7536/PC170127

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手性降冰片烯衍生物的制备及应用

曹堃, 袁贝, 刘学, 吴敏芳, 姚臻*

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Preparation and Applications of the Chiral Norbornene Derivatives

Kun Cao, Bei Yuan, Xue Liu, Minfang Wu, Zhen Yao*

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摘要

手性降冰片烯类衍生物是C5主馏分之一的（双）环戊二烯中一类重要的高附加值衍生产品，主要由环戊二烯和非对称的亲双烯体通过Diels-Alder反应制得。本文从合成手性降冰片烯衍生物的机理出发，重点介绍了在有/无催化剂条件下制备手性降冰片烯酯类、醛类、酮类和酰基(口恶)唑烷酮类衍生物时的收率和立体选择性等。由手性二醇、二酚或(口恶)唑啉与配位较强的铝、硼、铜、钛或镧系金属络合物等配位而成的手性催化剂有利于提高手性降冰片烯衍生物合成速度及其立体选择性。同时，本文针对近年来手性降冰片烯衍生物在光致变色的光学材料和阴离子、阳离子及复合离子交换膜领域中的应用进行了简要概述。最后，对其研究方向和应用前景进行了展望。

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

关键词

手性降冰片烯衍生物 / 环戊二烯 / 亲双烯体 / 狄尔斯-阿尔德反应

Key words

chiral norbornene derivatives / cyclopentadiene / dienophile / Diels-Alder reaction

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曹堃, 袁贝, 刘学, 吴敏芳, 姚臻*. 手性降冰片烯衍生物的制备及应用[J]. 化学进展, 2017, 29(6): 605-616 DOI:10.7536/PC170127

Kun Cao, Bei Yuan, Xue Liu, Minfang Wu, Zhen Yao*. Preparation and Applications of the Chiral Norbornene Derivatives[J]. Progress in Chemistry, 2017, 29(6): 605-616 DOI:10.7536/PC170127

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