4,4 '-disubstituted 1,2,3,4-tetrahydroisoquinolines from alkylation of a chiral non racemic lactam. An approach to the crinine-type alkaloids.

摘要

Enantiomerically pure 4,4-disubstituted tetrahydroisoquinolin-3-ones can be easily prepared by bis-alkylation of 1,2,3,4-tetrahyroisoquinolin-3-one 1 derived from (R)-(-)-phenylglycinol. The observed diastereoselectivity was explained by a rigid chelated intermediate. The obtained bis-alkylated products were used to prepare the ABC and ABD rings of the crinine alkaloid skeleton. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 23]