77250-64-7Relevant academic research and scientific papers
Enantioselective modification of the Pomeranz-Fritsch-Bobbitt synthesis of tetrahydroisoquinoline alkaloids synthesis of (-)-salsolidine and (-)-carnegine
Gluszynska, Agata,Rozwadowska, Maria D.
, p. 2359 - 2366 (2007/10/03)
(-)-Salsolidine 7 and (-)-carnegine 8 were prepared in 46 and 36% e.e., respectively, by enantioselective addition of methyllithium to the Pomeranz-Fritsch imine 13 in the presence of ligands 9-12, followed by acid-catalyzed cyclization and hydrogenolysis
AN ASYMMETRIC SYNTHESIS OF CHIRAL PHTHALIDES VIA CHIRAL LITHIATED OXAZOLINES
Meyers, A. I.,Hanagan, Mary Ann,Trefonas, L. M.,Baker, R. J.
, p. 1991 - 1999 (2007/10/02)
Chiral aromatic oxazolines were prepared for utilization in asymmetric C-C bonding reactions.Lithiation of aryloxazolines could not be accomplished directly but were efficiently lithiated via halogen metal exchange of the o-bromo derivative (16).The resulting lithio compound (9) reacted smoothly with carbonyls to give adducts 19 but with poor stereoselectivity.Hydrolysis gave the phthalides 4 in poor ee's (20-25percent).When the lithio-oxazolines 9 were transformed into 21, they now served as chiral electrophiles.Addition of organometallics to 21 gave, particularly with Grignard reagents, useful levels of asymmetric induction which, after hydrolysis, gave phthalides 4 in 40-80percent ee.
2-OXAZOLINES FROM AMIDES VIA IMIDATES
Meyers, A. I.,Hanagan, Mary Ann,Mazzu, Arthur L.
, p. 361 - 367 (2007/10/02)
Chiral oxazolines useful in asymmetric synthesis of o-substituted phthalides and benzoic acids are readily prepared from the benzamides via their imino ethers.
