M. Zhang, Jun-Xin Wang, Shun-qin Chang
Feb 1, 2020
Citations
0
Influential Citations
14
Citations
Journal
Chinese Chemical Letters
Abstract
Abstract A quinine-derived thiourea-catalyzed inter-/intramolecular Michael cycloaddition of chromone-oxindole/benzofuranone synthons with 3-substituted methylenebenzofuranones has been established, which constructed enantiomerically pure bispiro[benzofuran-oxindole/benzofuran-chromanone]s bearing five consecutive stereocenters including two spiro quaternary carton centers in good yields (up to 93%) with high diastereoselectivities (up to >20:1 dr) and good enantioselectivities (up to >99% ee). Moreover, this is the first example of bifunctional chromone-benzofuranone synthon directed organocatalytic tandem reaction, and also the first example of the bispiro[benzofuran-oxindole] and bispirobenzofuranone, potentially useful in medicinal chemistry.