1092491-82-1Relevant articles and documents
Chiral N-heterocyclic carbene-catalyzed formal [4+2] cycloaddition of ketenes with enones: Highly enantioselective synthesis of trans- And cis-δ-lactones
Zhang, Yan-Rong,Lv, Hui,Zhou, Di,Ye, Song
supporting information; experimental part, p. 8473 - 8476 (2009/10/15)
The chiral N-hetrocyclic carbenes (NHC)-catalyzed formal [4+2] cycloaddition of ketones with enones to give δ-lactones was reported. The results show that reaction at 0°C leads to better enantioselectivity and yield, while at -10°C result in slightly better enantioselectivity with lesser yield. It is also noted that the diasterometric ratios and enantiometric excess is improved by a single recrystallization from hexane/2-propanol 9:1. The cis-isomer of δ-lactones could be obtained with high diasteroselectivity and enantioselectivity by the in situ deprotonation-protonation after the NHC-catalyzed cycloaddition. The NHC-catalyzed [4+2] cycloaddition of ketones are possibly initiated by the nucleophilic addition of NHC to ketenes to give triazolium enolates.