Asymmetric induction using chiral 1,2,4-triazole and benzimidazole derivatives

被引:22
作者
Katritzky, AR [1 ]
Aslan, DC [1 ]
Leeming, P [1 ]
Steel, PJ [1 ]
机构
[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND
关键词
D O I
10.1016/S0957-4166(97)00155-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Lithiated N-substituted 1,2,4-triazoles 3 and 8 and benzimidazole 11 reacted with (1R)-fenchone to give derivatives 5c, 9 and 12 in good yields as single diastereoisomers. (S)-Lactic acid 16 reacted with o-phenylenediamine 15 to give optically pure (S)-2-(I-hydroxyethyl)benzimidazole 17 (85%). Ring closures converted the fenchone derivative 12 into novel tricyclic fused benzimidazoles 13 and 14, and converted oxazolidine derivative 17 into compound 18 in yields of 50-70% as single diastereoisomers. Lithiated derivative 18 was alkylated to give compound 19 as a single diastereoisomer in high yield. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1491 / 1500
页数:10
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