Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 11, Pages 5806-5810Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016439
Keywords
asymmetric catalysis; heterocycle; palladium; regioselectivity; spiroannulation
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Funding
- Tamaki Foundation
- Chugai Pharmaceuticals
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A novel Pd-0-catalyzed highly selective [3+2] spiroannulation reaction has been developed for rapid assembly of a new class of [5,5] spirocyclic carbo- and heterocycles. The regioselectivity of the reaction can be controlled by fine-tuning the Pd-pi-allyl intermediate, with excellent toleration of various coupling partners and enantioselectivities demonstrated through further transformations.
A novel Pd-0-catalyzed highly regio- and enantioselective [3+2] spiroannulation reaction has been developed for rapid assembly of a new class of [5,5] spirocyclic carbo- and heterocycles. Notably, the regioselectivity could be dominated by fine-tuning of the Pd-pi-allyl intermediate. An array of coupling partners could be well-tolerated with excellent regio-, and enantioselectivities. Moreover, the potential application of this reaction was exemplified by several further transformations.
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