Sulfinimine-Mediated Asymmetric Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines:: A Stereoselective Synthesis of cis- and trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline

被引:59
作者
Davis, FA [1 ]
Mohanty, PK [1 ]
Burns, DM [1 ]
Andemichael, YW [1 ]
机构
[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
关键词
D O I
10.1021/ol006654u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The highly diastereoselective addition of lateral lithiated o-tolunitriles to sulfinimines followed by treatment of the resulting sulfinamide with MeLi, hydrolysis, and reduction represents a concise new methodology for the asymmetric synthesis of 1,3-disubstituted tetrahydroisoquinolines.
引用
收藏
页码:3901 / 3903
页数:3
相关论文
共 22 条
[1]   The synthesis of 1-aminodihydroisoquinolines by an imine addition-cyclisation reaction. [J].
Beaton, H ;
Hamley, P ;
Tinker, AC .
TETRAHEDRON LETTERS, 1998, 39 (10) :1227-1230
[2]  
BRINGMANN G, 1993, LIEBIGS ANN CHEM, P877
[3]   ACETOGENIC ISOQUINOLINE ALKALOIDS .11. REGIOSELECTIVE AND ATROPOISOMERIC-SELECTIVE ARYL COUPLING TO GIVE NAPHTHYL ISOQUINOLINE ALKALOIDS - THE 1ST TOTAL SYNTHESIS OF (-)-ANCISTROCLADINE [J].
BRINGMANN, G ;
JANSEN, JR ;
RINK, HP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (10) :913-915
[4]  
Bringmann G., 1995, ALKALOIDS, V46, P127
[5]   Acylation and alkylation of 2-and 4-methylbenzonitrile [J].
Bunce, RA ;
Johnson, LB .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1999, 31 (04) :407-412
[6]  
CLARK RD, 1995, ORG REACTIONS, V47, P5
[7]   Asymmetric synthesis of 4-hydroxy-3-phenyltetrahydroisoquinolin derivatives using enantiopure sulfinimines (N-sulfinyl imines) [J].
Davis, FA ;
Andemichael, YW .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8627-8634
[8]  
Davis FA, 1998, CHEM SOC REV, V27, P13
[9]  
DAVIS FA, 1999, J ORG CHEM, V64, P1043
[10]  
Fanelli D. L., 1999, ORG SYNTH, V77, P50