23516-33-8

Upstream product

• 255851-57-1 (-)-(S)-O-cyclohex-2-enyl N-isopropylmonothiocarbamate 
• 255851-58-2 (R)-S-cyclohex-2-enyl N-isopropylmonothiocarbamate 
• 6426-26-2 (S)-cyclohex-2-en-1-ol 
• 75-16-1 methylmagnesium bromide 
• 492446-57-8 (-)-(R)-S-[3-(1-hydroxy-1-methylethyl)cyclohex-1-enyl] N-isopropylmonothiocarbamate 

Relevant academic research and scientific papers

The synthesis and configurational stability of enantioenriched α-thioallyllithium compounds and the stereochemical course of their electrophilic substitution

Deprotonation of enantioenriched S-allyl N-monoalkylmonothiocarbamates furnished the corresponding chiral lithium compounds. The α-thioallyllithium compounds 9 and 25 were found to be configurationally stable in THF solutions at -78 °C. These represent the first configurationally stable α-thio-substituted allyllithium compounds, and they can be utilized in asymmetric synthesis. Alkylations proceeded with stereo-inversion or in an anti-SE′ process, while addition to carbonyl compounds took place in a syn-SE′ process. Hydroxyalkylation products were employed as starting material for Ni0-catalyzed cross-coupling reactions.