3899-19-2Relevant articles and documents
Bisketene Equivalents as Diels-Alder Dienes
Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.
supporting information, p. 13328 - 13333 (2020/09/03)
2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.
Enantioselective rare-earth catalyzed quinone Diels-Alder reactions
Evans, David A.,Wu, Jimmy
, p. 10162 - 10163 (2007/10/03)
A highly enantioselective, quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazoline) (pybox) complexes has been developed. The reaction scope has been extended to include three quinones and five dienes, all of which e