Stereoselective intramolecular cycloadditions of homochiral N-alkenoyl aryl azides

被引:25
作者
Broggini, G
Garanti, L
Molteni, G
Pilati, T
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] Univ Insubria, Dipartimento Sci Chim Fis & Matemat, I-22100 Como, Italy
[3] CNR, Ctr Studio Relaz Tra Struttura & Reattivita Chim, I-20133 Milan, Italy
关键词
D O I
10.1016/S0957-4166(01)00190-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Starting from the commercially available (S)-1-phenylethylamine and L-alanine benzylester, we synthesised the homochiral N-alkenoyl aryl azides 2a-2d. The intramolecular cycloaddition of unsubstituted 2a and ab gave enantiopure 3.3a-dihydro-1,2,3-triazolo[1.5-a][1.4]benzodiazepine-4(6H)-ones 3a, 3b, 4a and 4b, while phenyl-substituted 2c and 2d gave enantiopure 1.1a-dihydro-2H-azirino[2.1-c][1,4]benzodiazepine-4(6H)-ones 5c, 5d, 6c and 6d. (C) 2001 Elsevier Science Ltd. All rights reserved.
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收藏
页码:1201 / 1206
页数:6
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