A step-wise reduction of nonracemic alpha-ketoamides to alpha-methine amides under mild conditions

doi:10.1016/j.tet.2016.03.001

	A step-wise reduction of nonracemic alpha-ketoamides to alpha-methine amides under mild conditions
	Lou, YZ; Cao, P; Cao, P (reprint author), Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China.; Wang, B; Wang, M; Jia, T; Liao, J
刊名	TETRAHEDRON
	2016
卷号	72 期号:16 页码:2042-2047
关键词	A-ketoamides Reduction Nonracemic Enantiomeric Specificity
DOI	10.1016/j.tet.2016.03.001
产权排序	1
文献子类	Article
英文摘要	A step-wise reductive method that converts nonracemic gamma-chiral alpha-ketoamides into amide derivatives was developed under mild conditions. The method involves a highly efficient three-step transformation including NaBH4-reduction, bromination and Pd/C hydrogenation reactions. As a consequence, a variety of nonracemic gamma-diaryl amides products were obtained in high overall yields with excellent enantiomeric specificity. The utility of the method is demonstrated through the concise formal synthesis of (+)-sertraline in good overall yield. (C) 2016 Elsevier Ltd. All rights reserved.
学科主题	Chemistry
语种	英语
资助机构	National Natural Science Foundation of China [21402186, 21572218] ; National Natural Science Foundation of China [21402186, 21572218] ; Western-Light Foundation of CAS ; Western-Light Foundation of CAS ; National Natural Science Foundation of China [21402186, 21572218] ; National Natural Science Foundation of China [21402186, 21572218] ; Western-Light Foundation of CAS ; Western-Light Foundation of CAS
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/28199]
专题	成都生物研究所_天然产物研究
通讯作者	Cao, P (reprint author), Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China.
推荐引用方式 GB/T 7714	Lou, YZ,Cao, P,Cao, P ,et al. A step-wise reduction of nonracemic alpha-ketoamides to alpha-methine amides under mild conditions[J]. TETRAHEDRON,2016,72(16):2042-2047.
APA	Lou, YZ.,Cao, P.,Cao, P .,Wang, B.,Wang, M.,...&Liao, J.(2016).A step-wise reduction of nonracemic alpha-ketoamides to alpha-methine amides under mild conditions.TETRAHEDRON,72(16),2042-2047.
MLA	Lou, YZ,et al."A step-wise reduction of nonracemic alpha-ketoamides to alpha-methine amides under mild conditions".TETRAHEDRON 72.16(2016):2042-2047.