Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 21, Pages 3782-3791Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700849
Keywords
[3+2] annulations; bispirooxindoles; ketimines; Lewis base catalysis; Morita-Baylis-Hillman carbonates; tetrasubstituted stereogenic centers
Categories
Funding
- National Natural Science Foundation of China [21572135, 21125206]
Ask authors/readers for more resources
Constructing chiral bispirooxindoles is difficult to achieve but highly attractive owing to their many potential applications in medicinal chemistry. Here we present an asymmetric [3+2] annulation reaction of Morita-Baylis-Hillman carbonates from isatins and isatin-based N-Boc-ketimines under the catalysis of a newly designed multifunctional 4-dimethylaminopyridine-type substance. The reaction shows high gamma-regioselectivity, producing highly complex 1,2-bispirooxindoles incorporating a dihydropyrrolidine motif in excellent yields with moderate to outstanding stereoselectivity (dr > 19: 1, up to > 99% ee). This protocol has been expanded to utilize trifluoromethyl-containing ketimines, delivering complicated architectures with fused and spirocyclic frameworks in modest enantioselectivity.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available