Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone

doi:10.1007/s40242-015-4440-8

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (4): 669-673.doi: 10.1007/s40242-015-4440-8

Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone

LIU Can, ZHOU Ya, YANG Liwen, YANG Nianfa, ZHANG Anlin

Key Laboratory of Environmentally Friendly Chemistry and Applications, Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. China

收稿日期:2014-11-21 修回日期:2015-03-20 出版日期:2015-08-01 发布日期:2015-05-04
通讯作者: YANG Nianfa E-mail:nfyang@xtu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21172186) and the Higher Education Doctoral Science Foundation of China(No.20134301110004).

Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone

LIU Can, ZHOU Ya, YANG Liwen, YANG Nianfa, ZHANG Anlin

Key Laboratory of Environmentally Friendly Chemistry and Applications, Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. China

Received:2014-11-21 Revised:2015-03-20 Online:2015-08-01 Published:2015-05-04
Contact: YANG Nianfa E-mail:nfyang@xtu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21172186) and the Higher Education Doctoral Science Foundation of China(No.20134301110004).

摘要/Abstract

摘要：

A new kind of optically active polymer bearing chiral amino alcohol was prepared by means of graft. The resulting grafted polymer was obtained as follows. First, the carbonyl of optically active helical poly(menthyl vinyl ketone)(poly-MVK) was reduced to hydroxyl group with lithium aluminum hydride as a reductant to yield poly(1-menthyl-2-propen-1-ol)(poly-MPO). Second, the hydroxyl group of poly-MPO reacted with epichlorohydrin to yield methyloxirane-loading poly-MPO[(poly-MPO)-MO]. Third, the(poly-MPO)-MO reacted with amine to produce optically active polymer bearing chiral amino alcohol[(poly-MPO)-APO]. The (poly-MPO)-APO was applied to the asymmetric addition of phenylacetylene to aromatic ketone. Good enantioselectivities were achieved and the catalyst could be recovered and reused 5 times with unchanged enantioselectivity and slightly decreased activity.

关键词: Chiral amino alcohol, Graft, Poly(menthyl vinyl ketone), Enantioselective addition

Abstract:

Key words: Chiral amino alcohol, Graft, Poly(menthyl vinyl ketone), Enantioselective addition

LIU Can, ZHOU Ya, YANG Liwen, YANG Nianfa, ZHANG Anlin. Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone[J]. 高等学校化学研究, 2015, 31(4): 669-673.

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Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone

Graft of Chiral Amino Alcohol onto Poly(menthyl vinyl ketone) and the Grafted Polymer's Inducement to the Asymmetric Addition of Phenylacetylene to Aromatic Ketone

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