Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines by Cascade Reaction between Aryl Nitriles, Silyldichloromethanes, and tert-Butanesulfinylimines
Huang, ZA (Huang, Ze-Ao); Liu, H (Liu, Hui); Lu, CD (Lu, Chong-Dao); Xu, YJ (Xu, Yan-Jun); Lu, CD
2015
发表期刊ORGANIC LETTERS
卷号17期号:16页码:4042-4045
摘要

The cascade coupling of aryl nitriles, silyldichloromethanes, and tert-butanesulfinylimines is described, in which silylciichloromothyl-lithiums, generated from silyldichloromethanes in the presence of lithium diisopropylamide, undergo nucleophilic addition with aryl nitriles and subsequent [1,3]-aza-Brook rearrangement to give dichlorocarbanions bearing alpha-N-silyl imine (or their 1-azaenolate equivalents), which are then trapped by tert-butanesulfinylimines via an aza-Darzons-type transformation, affording enantioenriched 2-chloro-2-aroylaziridines after acidic hydrolysis of the N-silyl imine group. The stereochemistry of this cascade reaction can be tuned by selecting appropriate silyl groups on the silyldichloromethanes and altering the order of addition of the imines and the hexamethylphosphoramide additive.

DOI10.1021/acs.orglett.5b01954
收录类别SCI
WOS记录号WOS:000360102900027
引用统计
被引频次:7[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.xjipc.cas.cn/handle/365002/5144
专题省部共建新疆特有药用资源利用重点实验室
通讯作者Lu, CD
作者单位1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China
2.Changji Univ, Dept Chem & Appl Chem, Changji 831100, Peoples R China
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GB/T 7714
Huang, ZA ,Liu, H ,Lu, CD ,et al. Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines by Cascade Reaction between Aryl Nitriles, Silyldichloromethanes, and tert-Butanesulfinylimines[J]. ORGANIC LETTERS,2015,17(16):4042-4045.
APA Huang, ZA ,Liu, H ,Lu, CD ,Xu, YJ ,&Lu, CD.(2015).Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines by Cascade Reaction between Aryl Nitriles, Silyldichloromethanes, and tert-Butanesulfinylimines.ORGANIC LETTERS,17(16),4042-4045.
MLA Huang, ZA ,et al."Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines by Cascade Reaction between Aryl Nitriles, Silyldichloromethanes, and tert-Butanesulfinylimines".ORGANIC LETTERS 17.16(2015):4042-4045.
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