XJIPC OpenIR  > 省部共建新疆特有药用资源利用重点实验室
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
Source PublicationORGANIC LETTERS
Volume17Issue:16Pages:4042-4045
Abstract

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
Indexed BySCI
WOS IDWOS:000360102900027
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5144
Collection省部共建新疆特有药用资源利用重点实验室
Corresponding AuthorLu, CD
Affiliation1.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
Recommended Citation
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.
Files in This Item:
File Name/Size DocType Version Access License
Stereoselective Synt(690KB)期刊论文作者接受稿开放获取CC BY-NC-SAView Application Full Text
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Huang, ZA (Huang, Ze-Ao)]'s Articles
[Liu, H (Liu, Hui)]'s Articles
[Lu, CD (Lu, Chong-Dao)]'s Articles
Baidu academic
Similar articles in Baidu academic
[Huang, ZA (Huang, Ze-Ao)]'s Articles
[Liu, H (Liu, Hui)]'s Articles
[Lu, CD (Lu, Chong-Dao)]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Huang, ZA (Huang, Ze-Ao)]'s Articles
[Liu, H (Liu, Hui)]'s Articles
[Lu, CD (Lu, Chong-Dao)]'s Articles
Terms of Use
No data!
Social Bookmark/Share
File name: Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines by Cascade Reaction between Aryl Nitriles, Silyldichloromethanes, and tert-Butanesulfinylimines.pdf
Format: Adobe PDF
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.