Enantioselective rhodium-catalyzed [4+2+2] cycloaddition of dienyl isocyanates for the synthesis of bicyclic azocine rings.
A highly enantioselective rhodium-catalyzed [4+2+2] cycloaddition of terminal alkynes and dienyl isocyanates has been developed. The cycloaddition provides a rapid entry to highly functionalized and enantioenriched bicyclic azocines. This reaction represents the first [4+2+2] cycloaddition strategy to construct nitrogen-containing eight-membered rings.
Yu
Robert T
RT
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Friedman
Rebecca Keller
RK
Rovis
Tomislav
T
D000480:Alkynes / Q000737:chemistry; D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D017953:Isocyanates / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000480:Alkynes; D001392:Azocines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D017953:Isocyanates; D012238:Rhodium