875612-06-9

Upstream product

• 201230-82-2 carbon monoxide 
• 766-77-8 Dimethylphenylsilane 
• 16079-23-5 (R)(S)-N-(1-methyl-1-ethyl-2-propinyl)-p-toluenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 18369-96-5 3-amino-3-methylpentyne 

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

Silylformylation - Fluoride-assisted aryl migration of acetylenic derivatives in a versatile approach to the synthesis of polyfunctionalised compounds

Polyfunctionalised aldehydes and dihydropyrans are prepared from easily available functionalised 1-alkynes through a two-step silylformylation/aryl migration sequence. The silylformylation process is performed under mild experimental conditions and affords the corresponding β-silylalkenals in high yields. The fluoride-promoted migration step occurs instantaneously with quantitative conversion. The chemo-, regio- and stereoselectivity can be modulated according to the nature and the position of the functional group on the acetylene precursors. When a good leaving group is present in the ω position of the aliphatic chain of the alkyne a cyclisation product is obtained, while α,β-unsaturated aldehydes are generated from propargylic tosylamides. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.