Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 50, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202212627
Keywords
Atropisomers; [2+2+2] Cycloaddition; Diels-Alder Reaction; Stereoselectivity; o-Quinodimethane
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Funding
- Swiss National Science Foundation [175746]
- University of Basel
- NCCR Molecular Systems Engineering [182895]
- European Research Council (ERC) under the European Union [101002471]
- European Research Council (ERC) [101002471] Funding Source: European Research Council (ERC)
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In this study, the accessibility of atropisomeric o-quinodimethanes and the enantioselective synthesis of their precursors were described. The catalyst-stereocontrolled [2+2+2] cycloaddition and subsequent stereospecific Diels-Alder reactions enabled the synthesis of enantioselective compounds with high selectivity.
o-Quinodimethanes have remarkable utility as reactive intermediates in Diels-Alder reactions, enabling significantly accelerated routes to complex polycyclic compounds. The discovery of different discrete precursors to thermally generate o-quinodimethanes thereby greatly augmented their availability and versatility. However, due to the required high temperatures and the immense reactivity of o-quinodimethanes, stereoselectivity to afford isomerically defined products still constitutes a critical challenge. Herein, we describe the accessibility of atropisomeric o-quinodimethanes, the enantioselective synthesis of their precursors, their remarkable configurational stability and the stereospecific transformation by the benzannulation of dienophiles. A catalyst-stereocontrolled [2+2+2] cycloaddition, the generation of o-quinodimethane atropisomers and ensuing stereospecific Diels-Alder reactions enabled enantioselectivities through these transient intermediates with of up to 96 : 4 e.r.
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