Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction

doi:10.1007/s40242-018-7364-2

高等学校化学研究 ›› 2018, Vol. 34 ›› Issue (2): 180-185.doi: 10.1007/s40242-018-7364-2

Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction

WANG Rui¹, WEI Zhonglin¹, GUO Jing¹, FENG Yusha¹, XU Enjie¹, DUAN Haifeng¹, LIN Yingjie¹, YANG Qingbiao¹, DU Jianshi², LI Yaoxian¹

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. China-Japan Union Hospital of Jilin University, Changchun 130031, P. R. China

收稿日期:2017-11-14 修回日期:2017-12-05 出版日期:2018-04-01 发布日期:2017-12-18
通讯作者: YANG Qingbiao,E-mail:yangqb@jlu.edu.cn;DU Jianshi,E-mail:dujianshi3043@163.com E-mail:yangqb@jlu.edu.cn;dujianshi3043@163.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21174052) and the Natural Science Foundation of Jilin Province of China(Nos.20160101311JC, 20170101105JC).

Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction

WANG Rui¹, WEI Zhonglin¹, GUO Jing¹, FENG Yusha¹, XU Enjie¹, DUAN Haifeng¹, LIN Yingjie¹, YANG Qingbiao¹, DU Jianshi², LI Yaoxian¹

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. China-Japan Union Hospital of Jilin University, Changchun 130031, P. R. China

Received:2017-11-14 Revised:2017-12-05 Online:2018-04-01 Published:2017-12-18
Contact: YANG Qingbiao,E-mail:yangqb@jlu.edu.cn;DU Jianshi,E-mail:dujianshi3043@163.com E-mail:yangqb@jlu.edu.cn;dujianshi3043@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21174052) and the Natural Science Foundation of Jilin Province of China(Nos.20160101311JC, 20170101105JC).

摘要/Abstract

摘要： Chiral organocatalysts of 4-adamantane amide based on L-proline with double hydrogen potential were synthesized and used in asymmetric aldol reactions. The reactions were evaluated in toluene under -20℃. A series of aldol products was obtained from moderate to good yields(up to 98%) with excellent diastereoselectivities(up to >99:1) and enantioselectivities(up to >99%). The aldol products in the system were separated by α-cyclodextrin via host-guest interaction and determined by chiral HPLC. The catalyst could be reused up to five times. The 4-substitution position played an important role in diastereoselectivity and enantioselectivity.

关键词: Prolinamide, Double hydrogen, Aldol reaction, Recycle, Cyclodextrin

Abstract: Chiral organocatalysts of 4-adamantane amide based on L-proline with double hydrogen potential were synthesized and used in asymmetric aldol reactions. The reactions were evaluated in toluene under -20℃. A series of aldol products was obtained from moderate to good yields(up to 98%) with excellent diastereoselectivities(up to >99:1) and enantioselectivities(up to >99%). The aldol products in the system were separated by α-cyclodextrin via host-guest interaction and determined by chiral HPLC. The catalyst could be reused up to five times. The 4-substitution position played an important role in diastereoselectivity and enantioselectivity.

Key words: Prolinamide, Double hydrogen, Aldol reaction, Recycle, Cyclodextrin

WANG Rui, WEI Zhonglin, GUO Jing, FENG Yusha, XU Enjie, DUAN Haifeng, LIN Yingjie, YANG Qingbiao, DU Jianshi, LI Yaoxian. Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction[J]. 高等学校化学研究, 2018, 34(2): 180-185.

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Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction

Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction

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