5911-60-4Relevant articles and documents
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.
Reductive electrophilic substitution of phthalans and ring expansion to isochroman derivatives
Azzena, Ugo,Demartis, Salvatore,Fiori, Maria Giovanna,Melloni, Giovanni,Pisano, Luisa
, p. 8123 - 8126 (2007/10/02)
Reductive cleavage of phthalan, 1a, with Li metal in the presence of a catalytic amount of naphthalene leads to the formation of a stable aromatic dilithium compound. The adducts of the latter with CO2, aldehydes or ketones undergo ring closure to isochroman derivatives, leading to ring expansion of the original heterocycle. The reductive electrophilic substitution procedure was successfully extended to the substituted phthalans 1b and 1c, to afford the corresponding isochroman-3-ones in satisfactory yields.