Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 12, Pages 4036-4040Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814403
Keywords
allylic compounds; annulations; cooperative catalysis; Lewis base; palladium
Categories
Funding
- NSFC [21572135]
- Sichuan University [2018SCUH0058]
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Auto-tandem catalysis (ATC), in which a single catalyst promotes two or more mechanistically different reactions in a cascade pattern, provides a powerful strategy to prepare complex products from simple starting materials. Reported here is an unprecedented auto-tandem cooperative catalysis (ATCC) for Morita-Baylis-Hillman carbonates from isatins and allylic carbonates using a simple Pd(PPh3)(4 )precursor. Dissociated phosphine generates phosphorus ylides and the Pd leads to pi-allylpalladiunz complexes, and they undergo a gamma-regioselective allylic-allylic alkylation reaction. Importantly, a cascade intramolecular Heck-type coupling proceeds to finally furnish spirooxindoles incorporating a 4-methylene-2-cyclopentene motif Experimental results indicate that both Pd and phosphine play crucial roles in the catalytic Heck reaction. In addition, the asymmetric versions with either a chiral phosphine or chiral auxiliary are explored, and moderate results are obtained.
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