175659-77-5Relevant academic research and scientific papers
Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol. A novel asymmetric route to 4-phenyl-1,2,3,4-tetrahydroisoquinolines
Philippe, Nicolas,Levacher, Vincent,Dupas, Georges,Quéguiner, Guy,Bourguignon, Jean
, p. 2185 - 2187 (2007/10/03)
(equation presented) Highly diastereoselective protonation of chiral lactam enolates of 4-substituted-1,4-dihydroisoquinolin-3-ones is reported. Protonation and alkylation processes of these lactam enolates derived from phenylglycinol occur with opposite diastereofacial selectivity. This diastereoselective protonation has been applied to the asymmetric synthesis of (4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 9 obtained in up to 97% ee.
4,4'-disubstituted 1,2,3,4-tetrahydroisoquinolines from alkylation of a chiral non racemic lactam. An approach to the crinine-type alkaloids
Roussi, Fanny,Quirion, Jean-Charles,Tomas, Alain,Husson, Henri-Philippe
, p. 10363 - 10378 (2007/10/03)
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 i
Diastereoselective alkylation of homochiral 1,2,3,4-tetrahydroisoquinolin-3-one. A potential route to enantiomerically pure 4-substituted tetrahydroisoquinolines
Philippe, Nicolas,Levacher, Vincent,Dupas, Georges,Duflos, Jack,Queguiner, Guy,Bourguignon, Jean
, p. 417 - 420 (2007/10/03)
Enantiomerically pure 1,4-dihydroisoquinolin-3-one 1 was prepared in four steps with an overall yield of 60%. Alkylation of the corresponding lactam enolate has been studied and has proven to be highly diastereoselective. Thus, 4-substituted-1,4-dihydroisoquinolin-3-ones 7a-d were obtained in high chemical yields with up to 97% diastereoisomeric excesses.
