Conformational Effects in Diastereoselective Aryne Diels−Alder Reactions: Synthesis of Benzo-Fused [2.2.1] Heterobicycles
Robert Webster
Mark Lautens
10.1021/ol9019869.s012
https://acs.figshare.com/articles/dataset/Conformational_Effects_in_Diastereoselective_Aryne_Diels_Alder_Reactions_Synthesis_of_Benzo_Fused_2_2_1_Heterobicycles/2821366
It was found that the diastereoselectivity of the Diels−Alder reaction between arynes and substituted furans is highly sensitive to substitution, which affects the reactive conformation. By varying the location of the groups on the diene partner, it is possible to obtain both excellent chemical yields and high stereoselectivity. This methodology offers rapid and convenient access to enantiomerically pure bicyclic scaffolds which are difficult to prepare by other means.
2009-10-15 00:00:00
bicyclic scaffolds
furan
diastereoselectivity
Aryne
enantiomerically
chemical yields
aryne
methodology
location
Diel
Heterobicycle
Synthesi
Conformational Effects
stereoselectivity
substitution
Diastereoselective
diene partner
access
reactive conformation