The direct functionalization of sp3 C–H bond via a tandem 1,5-hydride shift/ring closure1 attracted much attentions in the past years because it provided an alternative approach to synthesize heterocyclic compounds, especially for the construction of biologically interesting tetrahydroquinoline derivatives.2 Recently, we devoted to studying this type reaction by using chiral N,N’-dioxide-metal complexes3 as the catalysts, which could lower the activation barriers of 1,5-hydride shift and governing the stereoselectivity of the H-transfer and the subsequent ring closure. Various tetrahydroquinolines were obtained in good yields with high enantioselectivities catalyzed by a N,N'-dioxide-Co(II) complex.4 Meanwhile, a variety of spirooxindole tetrahydroquinoline derivatives were conducted with a chiral N,N'-dioxide-Sc(III) complex as the catalyst.5 Reference： 1. (a) Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2006, 45, 1683. (b) Pan, S. C. Beilstein J. Org. Chem. 2012, 8, 1374. (c) Wang, M. ChemCatChem, 2013, 5, 1291. (d) Peng, B.; Maulide, N. Chem.–Eur. J. 2013, 19, 13274. (e) Haibach, M. C.; Seidel, D. Angew. Chem., Int. Ed. 2014, 53, 5010. 2. Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031. 3. Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574. 4. Cao, W. D.; Liu, X. H.; Wang, W. T.; Lin, L. L.; Feng, X. M. Org. Lett. 2011, 13, 600. 5. Cao, W. D.; Liu, X. H.; Guo, J.; Lin, L. L.; Feng, X. M. Chem.–Eur. J. under review.

Catalytic asymmetric synthesis of tetrahydroquinolines via tandem 1,5-hydride transfer/Ring closure

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.