ASYMMETRIC-SYNTHESIS OF 1-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES .1. ADDITION OF CHIRAL PHENYLACETALDEHYDE ACETALS TO ACYLIMINES

被引:14
作者
WUNSCH, B
NERDINGER, S
机构
[1] Institut für Pharmazie, Lebensmittelchemie der Universität München, D-80333 Munich
关键词
D O I
10.1016/0040-4039(95)01716-U
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselectivity in the addition of the enantiomerically pure (2-bromophenyl)acetaldehyde acetals 3a-g to the acylimines 4a,b is investigated. Based on this reaction a novel asymmetric synthesis for the 1-phenyl-tetrahydroisoquinoline 8 is elaborated.
引用
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页码:8003 / 8006
页数:4
相关论文
共 24 条
[1]   CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].
ALEXAKIS, A ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511
[2]   MOLECULAR ASYMMETRY OF OLEFINS .2. ABSOLUTE CONFIGURATION OF TRANS-CYCLOOCTENE [J].
COPE, AC ;
MEHTA, AS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5626-&
[3]   PHENCYCLIDINE-LIKE EFFECTS OF TETRAHYDROISOQUINOLINES AND RELATED-COMPOUNDS [J].
GRAY, NM ;
CHENG, BK ;
MICK, SJ ;
LAIR, CM ;
CONTRERAS, PC .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1242-1248
[4]  
HASHIGAKI K, 1991, CHEM PHARM BULL, V39, P1126
[5]   EFFICIENT SYNTHESIS OF (R)-5-(2-HYDROXYETHYL)-2(5H)-FURANONE FROM (R)-MALIC ACID [J].
HERRADON, B .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :191-194
[6]   NEUROCHEMICAL AND ELECTROPHYSIOLOGICAL STUDIES ON FR115427, A NOVEL NONCOMPETITIVE NMDA RECEPTOR ANTAGONIST [J].
HODGKISS, JP ;
SHERRIFFS, HJ ;
COTTRELL, DA ;
SHIRAKAWA, K ;
KELLY, JS ;
KUNO, A ;
OHKUBO, M ;
BUTCHER, SP ;
OLVERMAN, HJ .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1993, 240 (2-3) :219-227
[7]  
HOPPE I, 1985, ANGEW CHEM, V97, P1066
[8]  
HUNGERBUHLER E, 1979, ANGEW CHEM, V12, P1025
[9]   SYNTHETIC STUDIES TOWARD MARINE TOXIC POLYETHERS .4. SYNTHESIS OF SEGMENT-A OF OKADAIC ACID VIA ANTI-SELECTIVITY BY HETEROCONJUGATE ADDITION [J].
ISOBE, M ;
ICHIKAWA, Y ;
BAI, D ;
GOTO, T .
TETRAHEDRON LETTERS, 1985, 26 (42) :5203-5206
[10]  
KUPFER R, 1984, SYNTHESIS-STUTTGART, P688