Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions.
Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C-H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearrangement provides access to trans-3,4-disubstituted hydroazulenes.
Bykowski
Darren
D
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Wu
Kou-Hui
KH
Doyle
Michael P
MP
D000475:Alkenes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011407:Propane / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D000475:Alkenes; D007783:Lactones; D014753:Vinyl Compounds; C516829:vinylcarbene; C516828:vinyldiazolactone; D002244:Carbon; D006859:Hydrogen; D011407:Propane