Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides

高等学校化学研究 ›› 2011, Vol. 27 ›› Issue (6): 958-962.

Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides

QI Heng-zhen, MO Shan-yan and XU Jia-xi*

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China

收稿日期:2011-01-13 修回日期:2011-02-13 出版日期:2011-11-25 发布日期:2011-11-07
通讯作者: XU Jia-xi E-mail:jxxu@mail.buct.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.20772005, 20972013), the Beijing Natural Science Foundation, China(No.2092022) and the Specialized Research Fund for the Doctoral Program of Higher Education, Ministry of Education of China.

Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides

QI Heng-zhen, MO Shan-yan and XU Jia-xi*

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China

Received:2011-01-13 Revised:2011-02-13 Online:2011-11-25 Published:2011-11-07
Contact: XU Jia-xi E-mail:jxxu@mail.buct.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20772005, 20972013), the Beijing Natural Science Foundation, China(No.2092022) and the Specialized Research Fund for the Doctoral Program of Higher Education, Ministry of Education of China.

摘要/Abstract

摘要： A series of trans-3-chloro-β-lactams was synthesized stereospecifically from imines and chloroacetyl chloride or a mixture of chloroacetyl chloride and nitroacetyl chloride, prepared from vinylidene chloride and a mixture of concentrated nitric acid and sulfuric acid, in the presence of triethylamine. The reaction of vinylidene chloride and the mixed acid was investigated. The formation mechanism of chloroacetyl chloride and nitroacetyl chloride and their reaction process with imines were proposed.

关键词: β-Lactam, Chloroacetyl chloride, Staudinger reaction, Stereoselectivity

Abstract: A series of trans-3-chloro-β-lactams was synthesized stereospecifically from imines and chloroacetyl chloride or a mixture of chloroacetyl chloride and nitroacetyl chloride, prepared from vinylidene chloride and a mixture of concentrated nitric acid and sulfuric acid, in the presence of triethylamine. The reaction of vinylidene chloride and the mixed acid was investigated. The formation mechanism of chloroacetyl chloride and nitroacetyl chloride and their reaction process with imines were proposed.

Key words: β-Lactam, Chloroacetyl chloride, Staudinger reaction, Stereoselectivity

QI Heng-zhen, MO Shan-yan and XU Jia-xi*. Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides[J]. 高等学校化学研究, 2011, 27(6): 958-962.

QI Heng-zhen, MO Shan-yan and XU Jia-xi*. Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides[J]. Chemical Research in Chinese Universities, 2011, 27(6): 958-962.

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Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides

Highly Stereoselective Synthesis of trans-3-Chloro-?-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides

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