Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected beta-Enamino Esters with Trichlorosilane

doi:10.1002/adsc.201501061

	Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected beta-Enamino Esters with Trichlorosilane
	Sun, J; Ye, JH; Wang, C; Chen, L; Wu, XJ; Zhou, L; Sun, J (reprint author), Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China.
刊名	ADVANCED SYNTHESIS & CATALYSIS
	2016
卷号	358 期号:7 页码:1042-1047
关键词	B-amino Esters Asymmetric Hydrosilylation Lewis Bases Reduction Trichlorosilane
DOI	10.1002/adsc.201501061
产权排序	1
文献子类	Article
英文摘要	Catalytic asymmetric reduction of N-unsubstituted beta-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted beta-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of beta-aryl- and beta-alkyl-substituted free beta-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.
学科主题	Chemistry
语种	英语
资助机构	Western Light Talents Training Program of Chinese Academy of Sciences ; Western Light Talents Training Program of Chinese Academy of Sciences ; National Natural Science Foundation of China [21272227, 21402185] ; National Natural Science Foundation of China [21272227, 21402185] ; Science & Technology Department of Sichuan Province [2012SZ0219] ; Science & Technology Department of Sichuan Province [2012SZ0219] ; Western Light Talents Training Program of Chinese Academy of Sciences ; Western Light Talents Training Program of Chinese Academy of Sciences ; National Natural Science Foundation of China [21272227, 21402185] ; National Natural Science Foundation of China [21272227, 21402185] ; Science & Technology Department of Sichuan Province [2012SZ0219] ; Science & Technology Department of Sichuan Province [2012SZ0219]
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/28202]
专题	成都生物研究所_天然产物研究
通讯作者	Wang, C; Sun, J (reprint author), Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China.
推荐引用方式 GB/T 7714	Sun, J,Ye, JH,Wang, C,et al. Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected beta-Enamino Esters with Trichlorosilane[J]. ADVANCED SYNTHESIS & CATALYSIS,2016,358(7):1042-1047.
APA	Sun, J.,Ye, JH.,Wang, C.,Chen, L.,Wu, XJ.,...&Sun, J .(2016).Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected beta-Enamino Esters with Trichlorosilane.ADVANCED SYNTHESIS & CATALYSIS,358(7),1042-1047.
MLA	Sun, J,et al."Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected beta-Enamino Esters with Trichlorosilane".ADVANCED SYNTHESIS & CATALYSIS 358.7(2016):1042-1047.