Gold-catalyzed stereoselective synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from diverse 1-oxo-4-oxy-5-ynes: a viable formal [4 + 2] cycloaddition on an s-trans-heterodiene framework.
We report a highly stereoselective Au-catalyzed synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from diverse 1-oxo-4-oxy-5-ynes. Formation of these highly strained anti-Bredt oxacycles implies the workability of an unprecedented 1,4-dipole of s-trans-methylene(vinyl)oxonium. This work reveals the feasibility of a formal [4 + 2] cycloaddition on an s-trans-heterodiene framework.
Teng
Tse-Min
TM
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, ROC.
Das
Arindam
A
Huple
Deepak B
DB
Liu
Rai-Shung
RS
D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D009942:Organometallic Compounds; D012834:Silver; D006046:Gold