4,4'-DISUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES FROM ALKYLATION OFA CHIRAL NON RACEMIC LACTAM - AN APPROACH TO THE CRININE-TYPE ALKALOIDS

Authors
ROUSSI F QUIRION JC TOMAS A HUSSON HP
Citation
F. Roussi et al., 4,4'-DISUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINES FROM ALKYLATION OFA CHIRAL NON RACEMIC LACTAM - AN APPROACH TO THE CRININE-TYPE ALKALOIDS, Tetrahedron, 54(35), 1998, pp. 10363-10378
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
35
Year of publication
1998
Pages
10363 - 10378
Database
ISI
SICI code
0040-4020(1998)54:35<10363:41FAO>2.0.ZU;2-X
Abstract
Enantiomerically pure 4,4-disubstituted tetrahydroisoquinolin-3-ones c an be easily prepared by bis-alkylation of 1,2,3,4-tetrahyroisoquinoli n-3-one 1 derived from (R)-(-)-phenylglycinol. The observed diastereos electivity was explained by a rigid chelated intermediate. The obtaine d bis-alkylated products were used to prepare the ABC and ABD rings of the crinine alkaloid skeleton. (C) 1998 Elsevier Science Ltd. All rig hts reserved.