144776-79-4

Upstream product

• 6340-49-4 1-(1,1-dimethyl-2-propynyl)-piperidine 
• 201230-82-2 carbon monoxide 
• 766-77-8 Dimethylphenylsilane 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 16079-17-7 N-(1,1-dimethyl-prop-2-ynyl)-4-methyl-benzenesulfonamide 
• 128549-31-5 (Z)-2-(1-hydroxy-1-methylethyl)-3-dimethylphenylsilylpropenal 
• 1604-29-1 1,1-dimethyl-2-propynyl acetate 
• 2978-58-7 1,1-dimethylprop-3-ynylamine 

Relevant academic research and scientific papers

Silylation-desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams

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.

Silylformylation-desilylation of propargyl amides: Synthesis of α,β-unsaturated aldehydes

α,β-Unsaturated aldehydes are prepared from easily available propargyl amides through a two-step sequence of silylformylation-desilylation reactions. The substituent on the nitrogen atom markedly influences both reactions, β-silylalkenals being formed in

Rhodium-catalyzed transformation of propargyl alcohol derivatives to 2-silylmethyl-2-alkenals

Propargyl-type alcohols (6) and the corresponding esters of carbonic acid (4) or acetic acid (5) react with two equivalents of Me2PhSiH in the presence of catalytic amounts of Rh4(CO)12 under CO pressure at 100°C to give 2

Rhodium catalyzed transformation of propargylamines to 2-silylmethyl-2-alkenals: Formal silylformylation of allenes

Propargylamines are effectively transformed to 2-dimethylphenylsilylmethyl-2-alkenals by the interaction of two equivalents of Me2PhSiH under silylformylation conditions catalyzed by Rh4(CO)12. The products are not obtained directly by silylformylation of the corresponding allenes.