Premium
Use of the Diels–Alder Cycloaddition of Tetracyclone and Internal Aryl Acetylenes for the Synthesis of Functionalized Atropisomeric Biaryls
Author(s) -
Hapke Marko,
Gutnov Andrey,
Weding Nico,
Spannenberg Anke,
Fischer Christine,
BenkhäuserSchunk Christian,
Heller Barbara
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901080
Subject(s) - cycloaddition , chemistry , atropisomer , diastereomer , aryl , yield (engineering) , enantiomer , organic chemistry , diels–alder reaction , combinatorial chemistry , catalysis , alkyl , materials science , metallurgy
The Diels–Alder cycloaddition reaction of tetracyclone and functionalized, internal aryl acetylenes gave access to a number of bulky atropisomeric biaryls in good to excellent yield. The synthesis is convenient and yields the pure biaryls without tedious work‐up and purification procedures. Exemplarily the atropisomers have been resolved via the diastereomers in an easy and efficient manner to yield the enantiomers.