77220-06-5Relevant 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.
Reactions of Trialkylsilyl Trifluoromethanesulfonates, VIII. - Synthesis of O-(Trimethylsilyl)ketene O,N-Acetals, 2,5-Bis(trimethylsiloxy)pyrroles, -furans, and -thiophenes
Frick, Ulrich,Simchen, Gerhard
, p. 839 - 846 (2007/10/02)
Ketene O,N-acetals 3, 4, 6, 8 are obtained from N,N-diarylcarboxamides and N-acetylheterocycles 5, 7 by silylation with trimethylsilyl triflate (2) in the presence of triethylamine.Analogous reactions of carboxamides 9 and N-acyllactams 11 yield the keten
