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N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis
引用本文:SongQingWANG OmarA.IBRAHIMI PanLI KangZHAO. N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis[J]. 中国化学快报, 2004, 15(1): 1-4
作者姓名:SongQingWANG OmarA.IBRAHIMI PanLI KangZHAO
作者单位:[1]CollegeofPharmaceuticalsandBiotechnology,TianjinUniversity,Tianjin300072 [2]DepartmentofChemistry,NewYorkUniversity,NewYork,NY10003,USA
摘    要:Intramolecular cyclization of N-alkoxyl amines are studied for the stereoselective preparation of 2, 4-disubstituted pyrrolidine derivatives. Reduction of oximes under acidic conditions by NaBH3CN afforded the corresponding nucleophilic hydroxylamine derivatives,which subsequently cyclized via SN2‘ mechanism to give the desired N-alkoxyl pyrrolidines.

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N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis
Song Qing WANG, Omar A. IBRAHIMI, Pan LI, Kang ZHAO College of Pharmaceuticals and Biotechnology,Tianjin University,Tianjin. N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis[J]. Chinese Chemical Letters, 2004, 15(1): 1-4
Authors:Song Qing WANG   Omar A. IBRAHIMI   Pan LI   Kang ZHAO College of Pharmaceuticals  Biotechnology  Tianjin University  Tianjin
Affiliation:Song Qing WANG,1 Omar A. IBRAHIMI,2 Pan LI,2 * Kang ZHAO1* 1 College of Pharmaceuticals and Biotechnology,Tianjin University,Tianjin 300072 2 Department of Chemistry,New York University,New York,NY 10003,USA
Abstract:Intramolecular cyclization of N-alkoxyl amines are studied for the stereoselective preparation of 2, 4-disubstituted pyrrolidine derivatives. Reduction of oximes under acidic conditions by NaBH3CN afforded the corresponding nucleophilic hydroxylamine derivatives, which subsequently cyclized via SN2' mechanism to give the desired N-alkoxyl pyrrolidines.
Keywords:SN' reaction   pyrrolidines   oxime   hydroxylamine.
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