556799-86-1Relevant academic research and scientific papers
Redox-neutral synthesis of β-amino aldehydes from imines by an alkynylation/hydration sequence
Labonne, Aurelie,Zani, Lorenzo,Hintermann, Lukas,Bolm, Carsten
, p. 5704 - 5708 (2008/02/09)
(Chemical Equation Presented) N-Protected β-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of
Silylation-desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams
Aronica, Laura Antonella,Valentini, Giulia,Caporusso, Anna Maria,Salvadori, Piero
, p. 6843 - 6854 (2008/02/07)
Propargyl functionalised β-silylalkenals were easily prepared starting from suitable propargyl compounds by a silylformylation process. In particular the use of propargyl tosyl amides allowed the synthesis of α,β-unsaturated aldehydes through a two-step sequence of silylformylation-desilylation reactions. TBAF was employed to induce the desilylation process that was performed under very mild experimental conditions and occurred along with an elimination step of the tosylamido moiety affording 2-methylaryl-2-alkenals with good yields and stereoselectivity. When the tosyl amides were reacted with a hydrosilane in the presence of catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) α-silylmethylene-β-lactams were synthesised through a silylcarbocyclisation process. A high chemoselectivity towards the β-lactam was observed when dialkyl propargyl amides were employed. The obtained β-lactams were easily transformed into the corresponding methylaryl-β-lactams by fluoride induced aryl migration-desilylation with total retention of configuration of the migrating group and complete stereoselectivity towards the more stable β-lactam (E)-isomer.
