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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); Lu, CD
2016
发表期刊ORGANIC LETTERS
卷号18期号:4页码:880-883
摘要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
收录类别SCI
WOS记录号WOS:000370768200064
引用统计
被引频次:13[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/365002/4355
专题资源化学研究室
通讯作者Lu, CD
作者单位Chinese 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
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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 ,&Lu, CD.(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.
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