142467-44-5

Upstream product

• 155880-59-4 (Z)-(2S)-1-Nitro-2-<(2-phenylpropyl)thio>-1-propene 
• 129396-58-3 (S)-2-phenylpropanethiol 

Downstream Products

• 155880-62-9 (1S,4R,5S,6R)-5-Methyl-6-nitro-5-((S)-(S)-2-phenyl-propane-1-sulfinyl)-bicyclo[2.2.1]hept-2-ene 
• 142467-50-3 [(S)-2-((S)-(1S,6R)-1,3-Dimethyl-6-nitro-cyclohex-3-enesulfinyl)-1-methyl-ethyl]-benzene 
• 142467-51-4 [(S)-2-((S)-(1S,6R)-1,4-Dimethyl-6-nitro-cyclohex-3-enesulfinyl)-1-methyl-ethyl]-benzene 
• 142467-49-0 [(S)-1-Methyl-2-((S)-(1S,6R)-1,3,4-trimethyl-6-nitro-cyclohex-3-enesulfinyl)-ethyl]-benzene 
• 155880-64-1 (1S,4R,5S,6R)-5-Methyl-6-nitro-5-((S)-2-phenyl-propane-1-sulfonyl)-bicyclo[2.2.1]hept-2-ene 
• 142467-48-9 [(S)-2-((S)-(1S,5R,6R)-1,5-Dimethyl-6-nitro-cyclohex-3-enesulfinyl)-1-methyl-ethyl]-benzene 

Relevant academic research and scientific papers

Diastereoselective Diels-Alder Cycloadditions with Chiral 1-(Alkylsulfinyl)-2-nitroalkenes

Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric cycloaddition.Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids.Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure.Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than the E-dienophiles 5 and 6.