期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 25, 页码 13913-13917出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202102842
关键词
bicyclo[3; 1; 0]hexane; cascade annualtions; chemoselectivity; double deprotonation strategy; palladium– trimethylenemethane
资金
- NSFC [21971166, 21901169, 21931006, 21921002]
The chemoselective activation of Tsuji's 2-(cyanomethyl)allyl carbonates to generate palladium-trimethylenemethane 1,3-dipoles can be realized in the presence of Morita-Baylis-Hillman carbonates from activated ketones. The subsequent cascade annulations lead to the formation of complex frameworks with good to excellent enantioselectivity, while a similar annulation sequence using benzoyl aldehyde-derived substrates produces fused cyclopenta[b]furan architectures.
Here we report that the chemoselective activation of Tsuji's 2-(cyanomethyl)allyl carbonates to generate the palladium-trimethylenemethane 1,3-dipoles via a deprotonation strategy can be realized in the presence of Morita-Baylis-Hillman carbonates from substantial activated ketones. The following S(N)2 '-addition enables the formation of new 1,3-dipole species having an activated alkene moiety through a second deprotonation process, which then undergo cascade [1+2]/[3+2] annulations to furnish complex bicyclic [3.1.0]hexane frameworks having three contiguous quaternary stereogenic centers with good to excellent enantioselectivity. Moreover, by using benzoyl aldehyde-derived substrates, a [1+4]/[3+2] annulation sequence is similarly developed to produce fused cyclopenta[b]furan architectures.
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