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

Abstract

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]. Chemical Research in Chinese Universities, 2018, 34(2): 180-185.

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