gem-diborylalkenes: Their Diels-Alder transformation

1,1-Bisboronate species are a bisnucleophilic geminated-organometallic equivalent, which is considered to be one of the most valuable reagents in modern organic synthesis, providing rapid access to a wide array of transformations including the construction of C–C and C–heteroatom bonds. ^[1][2] In my research we describe the use of gem-diborylalkenes as dienophile-reactive groups for Diels-Alder reaction, which is explored for the first time. These reactions provide an efficient and general method for the conversion of gem-diborylalkenes to rapidly access 1,1-bisborylalkanes. Their novel reactivity toward the [4+2] cycloadditions scenario will forge a new class of transformations, where research is still beginning to develop.

1. Nallagonda; K. Padala; A. Masarwa Org. Biomol. Chem. 2018, 16, 1050-1064.
2. Royes; A. B. Cuenca; E. Fernández Eur. J. Org. Chem. 2018, 2728.