Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C-H bond insertion.
A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C-H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.
Department of Chemistry, University of Houston, 136 Fleming Building, Houston, Texas 77204-5003, USA.
Santa
S
Jansone-Popova
Jeremy A
JA
May
D000480:Alkynes / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D004952:Esters; D007659:Ketones; D011083:Polycyclic Compounds; C030011:carbene; D008697:Methane