Highly enantioselective conjugate addition of 1-bromonitroalkanes to α,β-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine
Highly enantioselective conjugate addition of 1-bromonitroalkanes to α,β-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine
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DOI：
10.1016/j.tet.2009.03.055
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发表时间：
2009-05-23
期刊：
影响因子：
2.1
通讯作者：
Yan, Ming
中科院分区：
文献类型：
--
作者：
Dong, Li-ting;Lu, Rui-jiong;Yan, Ming
Asymmetric conjugate addition of 1-bromonitroalkanes to alpha,beta-unsaturated ketones was studied using chiral primary amines as the catalysts. 9-Amino-9-deoxyepiquinine was found to be highly efficient catalyst for the transformation. 4-Bromo-4-nitroketones were obtained with excellent enantioselectivities (97-99% ee) and good yields (61-99%) for a variety of alkyl vinyl ketones. The product could be further debrominated with Bu3SnH/AlBN to provide chiral 4-nitroketones in good yield and without loss of the optical purity. (C) 2009 Elsevier Ltd. All rights reserved.
