Domino Synthesis of Benzo-Fused β,γ-Unsaturated Ketones from Alkenylboronic Acids and <i>N</i>‑Tosylhydrazone-Tethered Benzonitriles Manuel Plaza Miguel Paraja Lucía Florentino Carlos Valdés 10.1021/acs.orglett.8b03705.s001 https://acs.figshare.com/articles/journal_contribution/Domino_Synthesis_of_Benzo-Fused_-Unsaturated_Ketones_from_Alkenylboronic_Acids_and_i_N_i_Tosylhydrazone-Tethered_Benzonitriles/7583702 The transition-metal-free domino reaction between alkenylboronic acids and <i>N</i>-tosylhydrazones from <i>o</i>-(2-oxoalkyl)- and <i>o</i>-(3-oxoalkyl)­benzonitriles leads to β,γ-unsaturated indanones and tetralones featuring an α-“all-carbon” quaternary center. The employment of derivatives of α-substituted cyclopentanones and cyclohexanones led to the stereoselective preparation of β,γ-unsaturated tetrahydro­cyclo­penta­[<i>a</i>]­inden-8­(1<i>H</i>)-ones, hexahydro­fluorenones, and hexahydro­anthracenones as <i>cis</i>-fused single stereoisomers. A domino sequence involving diazo compound formation/reductive alkenylation/1,3-borotropic rearrangement/intramolecular bora-aza-ene reaction is proposed to justify the formation of the products as well as the stereoselectivity. 2019-01-14 12:48:27 alkenylboronic acids hexahydro oxoalkyl transition-metal-free domino reaction stereoselective preparation domino Synthesis Alkenylboronic Acids domino sequence formation