Enantioselective synthesis of 1-aryltetrahydroisoquinolines.
1-Aryltetrahydroisoquinolines (1-arylTHIQs) are important structural motifs in many alkaloids and biologically active compounds. Ligand 2a promotes the enantioselective addition of arylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield (S)-1-arylTHIQs in 97-99% ee. Pinacol arylboronic esters are the optimal precursors for the arylzinc reagents. This method is applied to the enantioselective synthesis of Solifenacin.
Wang
Sa
S
Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA.
Onaran
M Burak
MB
Seto
Christopher T
CT
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D004952:Esters; D044005:Tetrahydroisoquinolines