Abstract
Preparation of functionalized 3,4-dihydroisoquinolines 17a– j from ( S)- N-methoxy- N-methyl-1-[( R)-1-phenylethyl]aziridine-2-carboxamide 4 is an effective route for the synthesis of 3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinolin-4-ols. Stereoselective reduction of the cyclic imines 17a– j resulted in (1 S,3 S,4 R)-4-( tert-butyldimethylsilyl-oxy)-3-[( tert-butyldimethylsilyloxy)methyl]-6,7-dimethoxy-1,2-disubstituted-1,2,3,4-tetrahydroisoquinolines and the desilylation of the TBS groups afforded (1 S,3 S,4 R)-3-(hydroxymethyl)-6,7-dimethoxy-1,2-disubstituted-1,2,3,4-tetrahydroisoquinolin-4-ols 19a– i in good yields. Also, an asymmetric synthesis of novel tetracyclic 3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinolin-4-ols 23 and 25 was successfully achieved via Pd-catalyzed N-arylation and C–C coupling reaction.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
