10.1021/ol047725i.s003
Phillip Pelphrey
Phillip
Pelphrey
Jerry Jasinski
Jerry
Jasinski
Ray J. Butcher
Ray J.
Butcher
Dennis L. Wright
Dennis L.
Wright
Oxabicyclo[3.2.1]octane Derivatives as
Highly Reactive Dienophiles: Synthesis
of Bicyclo[5.<i>n</i>.0] Systems
American Chemical Society
2005
bicyclo
bridged alkenes
reaction proceeds
homoconjugation effects
stereochemical control
2005-02-03 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Oxabicyclo_3_2_1_octane_Derivatives_as_Highly_Reactive_Dienophiles_Synthesis_of_Bicyclo_5_i_n_i_0_Systems/3302518
We have developed highly versatile, homochiral oxabicyclo[3.2.1]octadiene building blocks for the synthesis of natural products. We have
found that these bridged alkenes undergo exceptionally facile Diels−Alder reactions and react faster than several well studied bicyclo[2.2.1]heptene dienophiles. The reaction proceeds with high levels of stereochemical control and in very good to excellent yields, providing access
to bicyclo[5.4.0]undecane and bicyclo[5.3.0]decane systems. This reactivity is attributed to strain and homoconjugation effects.