XJIPC OpenIR  > 资源化学研究室
Diethyl Phosphite Initiated Coupling of alpha-Ketoesters with Imines for Synthesis of alpha-Phosphonyloxy-beta-amino Acid Derivatives and Aziridine-2-carboxylates
Jiang, J (Jiang, Jin); Liu, H (Liu, Hui); Lu, CD (Lu, Chong-Dao); Xu, YJ (Xu, Yan-Jun)
2016
Source PublicationORGANIC LETTERS
ISSN1523-7060
Volume18Issue:4Pages:880-883
Abstract

Coupling of alpha-ketoesters with imines initiated by diethyl phosphite in the presence of alkaline metal hexamethyldisilazides is reported. Base-promoted addition of diethyl phosphite to a-ketoesters, followed by [1,2]-phosphonate/phosphate rearrangement, generates alpha-phosphonyloxy enolates that are subsequently intercepted by imines. The use of suitable azomethine coupling partners allows selective construction of syn-alpha-hydroxy-beta-amino acid derivatives or trans-aziridine-2-carboxylates in high yields with excellent diastereoselectivities.

DOI10.1021/acs.orglett.6b00273
Indexed BySCI
WOS IDWOS:000370768200064
Citation statistics
Cited Times:16[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/4355
Collection资源化学研究室
AffiliationChinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China;Univ Chinese Acad Sci, Urumqi 830011, Peoples R China
Recommended Citation
GB/T 7714
Jiang, J ,Liu, H ,Lu, CD ,et al. Diethyl Phosphite Initiated Coupling of alpha-Ketoesters with Imines for Synthesis of alpha-Phosphonyloxy-beta-amino Acid Derivatives and Aziridine-2-carboxylates[J]. ORGANIC LETTERS,2016,18(4):880-883.
APA Jiang, J ,Liu, H ,Lu, CD ,&Xu, YJ .(2016).Diethyl Phosphite Initiated Coupling of alpha-Ketoesters with Imines for Synthesis of alpha-Phosphonyloxy-beta-amino Acid Derivatives and Aziridine-2-carboxylates.ORGANIC LETTERS,18(4),880-883.
MLA Jiang, J ,et al."Diethyl Phosphite Initiated Coupling of alpha-Ketoesters with Imines for Synthesis of alpha-Phosphonyloxy-beta-amino Acid Derivatives and Aziridine-2-carboxylates".ORGANIC LETTERS 18.4(2016):880-883.
Files in This Item:
File Name/Size DocType Version Access License
Diethyl Phosphite In(397KB)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
[Jiang, J (Jiang, Jin)]'s Articles
[Liu, H (Liu, Hui)]'s Articles
[Lu, CD (Lu, Chong-Dao)]'s Articles
Baidu academic
Similar articles in Baidu academic
[Jiang, J (Jiang, Jin)]'s Articles
[Liu, H (Liu, Hui)]'s Articles
[Lu, CD (Lu, Chong-Dao)]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Jiang, J (Jiang, Jin)]'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: Diethyl Phosphite Initiated Coupling of α-Ketoesters with Imines for Synthesis of α-Phosphonyloxy-β-amino Acid Derivatives and Aziridine-2-carboxylates.pdf
Format: Adobe PDF
All comments (0)
No comment.
 

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