Synthesis and Optical Properties of Helical Poly[(S)-3-hydroxyl- diphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl] and Its Use in Asymmetric Hetero-Diels-Alder Reaction

doi:10.6023/cjoc201510038

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 812-817.DOI: 10.6023/cjoc201510038 Previous Articles Next Articles

ARTICLE

螺旋聚[(S)-3-(二苯羟甲基)-3'-乙烯基-2,2'-二羟基-1,1'-联萘]的合成、光学性质及其在杂-Diels-Alder反应中的不对称诱导

晏瑾懿, 阳珠生, 阳年发

湘潭大学化学学院环境友好化学与应用省部共建教育部重点实验室湘潭 411105

收稿日期:2015-10-29 修回日期:2015-12-10 发布日期:2015-12-15
通讯作者: 阳年发 E-mail:nfyang@xtu.edu.cn
基金资助:
国家自然科学基金(No.21172186)和高等学校博士学科点专项科研基金(No.20134301110004)资助项目.

Synthesis and Optical Properties of Helical Poly[(S)-3-hydroxyl- diphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl] and Its Use in Asymmetric Hetero-Diels-Alder Reaction

Yan Jinyi, Yang Zhusheng, Yang Nianfa

Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105

Received:2015-10-29 Revised:2015-12-10 Published:2015-12-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172186) and the Higher Education Doctoral Science Foundation of China (No. 20134301110004).

1. Synthesis and Optical Properties of Helical Poly[(S)-3-hydroxyl- diphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl] and Its Use in Asymmetric Hetero-Diels-Alder Reaction.PDF(1270KB)

Abstract

A novel binaphthol-based monomer, 3-hydroxydiphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl was synthesized and polymerized using azodiisobutyrodinitrile (AIBN) as an initiator to afford the polymer P-5. Polarimetry, UV-Vis and circular dichroism spectroscopy characterizations indicated that the polymer existed in the form of one-handed helical structure in solution. The application of helical polymer P-5 in catalytic asymmetric hetero-Diels-Alder (HDA) reaction between benzaldehyde and Danishefsky's diene has been studied, resulting in the target product with 71% ee. P-5can be easily recovered and reused without loss of catalytic activity.

Key words: synthetichelical polymer, binaphthyl, hetero-Diels-Alder reaction, asymmetric catalysis

Cite this article

Yan Jinyi, Yang Zhusheng, Yang Nianfa. Synthesis and Optical Properties of Helical Poly[(S)-3-hydroxyl- diphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl] and Its Use in Asymmetric Hetero-Diels-Alder Reaction[J]. Chin. J. Org. Chem., 2016, 36(4): 812-817.

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螺旋聚[(S)-3-(二苯羟甲基)-3'-乙烯基-2,2'-二羟基-1,1'-联萘]的合成、光学性质及其在杂-Diels-Alder反应中的不对称诱导

Synthesis and Optical Properties of Helical Poly[(S)-3-hydroxyl- diphenylmethyl-3'-vinyl-2,2'-dihydroxy-1,1'-binaphthyl] and Its Use in Asymmetric Hetero-Diels-Alder Reaction

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