Lewis acid-mediated nucleophilic alkylations on chiral [6,3a,4]oxadiazaindano[5,4-a]isoquinolines. Asymmetric synthesis of 1-alkyl substituted tetrahydroisoquinolines

被引:36
作者
Yamazaki, N [1 ]
Suzuki, H [1 ]
Aoyagi, S [1 ]
Kibayashi, C [1 ]
机构
[1] TOKYO UNIV PHARM & LIFE SCI,SCH PHARM,HACHIOJI,TOKYO 19203,JAPAN
关键词
D O I
10.1016/0040-4039(96)01337-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lewis acid-mediated nucleophilic alkylation of the chiral [6,3a,4]oxadiaza-indano[5,4-a]isoquinoline derivatives with various organometallic reagents leads to highly enantioselective synthesis of 1-alkyl substituted tetrahydroisoquinolines. This methodology was applied to the asymmetric synthesis of (-)-salsolidine and (+)-O-methylarmepavine. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6161 / 6164
页数:4
相关论文
共 15 条
[11]  
SUZUKI H, 1995, TETRAHEDRON LETT, V36, P6709, DOI 10.1016/0040-4039(95)01358-O
[12]  
TAKAHASHI H, 1991, CHEM PHARM BULL, V39, P836
[13]   ALKALOIDS FROM DISCARIA-SERRATIFOLIA [J].
TORRES, R ;
DELLEMONACHE, F ;
BATTISTAMARINIBETTOLO, G .
JOURNAL OF NATURAL PRODUCTS, 1979, 42 (04) :430-431
[14]  
YAMAMOTO Y, 1991, SYNLETT, P339
[15]   ASYMMETRIC-SYNTHESIS OF 1-ALKYLTETRAHYDROISOQUINOLINES USING CHIRAL OXAZOLO[2,3-A]TETRAHYDROISOQUINOLINES [J].
YAMATO, M ;
HASHIGAKI, K ;
QAIS, N ;
ISHIKAWA, S .
TETRAHEDRON, 1990, 46 (17) :5909-5920