Journal
ACS CATALYSIS
Volume 6, Issue 2, Pages 769-774Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02483
Keywords
C(sp(3))-H activation; adamantane; rimantadine; regioselectivity; stereoselectivity
Categories
Funding
- Chinese NSF [81430080, 81125021]
- Major State Basic Research Development Program [2015CB910603]
- SIMM [CASIMM0120154002/2002]
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Stereoselective functionalization of the adamantyl bridge methylene C(sp(3))-H bonds is a rather appealing, yet challenging strategy due to the bulky and unactivated nature. Here we present a palladium-catalyzed C(sp(3))-H arylation/hetereoarylation of the antivirus drug rimantadine with the picolinamide moiety as the bidentate directing group and a mono-N-protected amino acid (MPAA) as the ligand. Multisubstituted rimantadine substrates and diverse aryl/heteroaryl iodides are well tolerated, optically pure arylated rimantadine derivatives have been synthesized in high regio- and diastereoselectivity that compound space for further pharmaceutical research.
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