Substrate-controlled [4+1] and [3+2] annulations of ninhydrin-derived Morita-Baylis-Hillman carbonates to access polysubstituted furans and cyclopentenes.

Abstract

The effective and mild [4+1] annulation of ninhydrin-derived MBH carbonates with α,β-unsaturated ketones has been developed, providing a wide range of multisubstituted furans in high yields (up to 90%) with excellent β-regioselectivities. In contrast, the polysubstituted cyclopentenes bearing dispiro-bisindanedione motifs were obtained via classical [3+2] annulations by employing ninhydrin-derived MBH carbonates with 2-arylidene-1,3-indandiones under the same catalytic conditions. Furthermore, the structures of two kinds of cycloadducts were straightforwardly confirmed through X-ray diffraction analysis.