Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 26, Pages 7860-7864Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804160
Keywords
cycloaddition; palladium; relay catalysis; spiro compounds; umpolung
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Funding
- Ministry of Education of Singapore [R-143-000-613-112]
- A*STAR SERC [R-143-000-648-305]
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Reported herein is the divergent syntheses of [5,5] and [6,5] spiro-heterocycles under Lewis-acid-assisted palladium catalysis. In particular, an unprecedented switch from alkoxide-pi-allyl to dienolate reactivity was achieved by the use of palladium-titanium relay catalysis, and represents umpolung reactivity of vinylethylene carbonates. This method uses a simple procedure and commercially available catalysts, and delivers both classes of spiro-heterocycles, bearing three contiguous stereocenters, in high yield and uniformly excellent diastereoseledivity.
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