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