316830-92-9

Upstream product

• 221493-41-0 (S)-N-<(aminomethylene)-4-methoxy-2,3,6-trimethylbenzenesulfonamide>-3-amino-7-methyl-6-octenol 
• 221493-39-6 N-[1-[(S)-1-(2-Hydroxy-ethyl)-5-methyl-hex-4-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide 
• 221493-37-4 S,S-dimethyl N-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-carbonimidodithioate 
• 162145-93-9 (S)-3-amino-7-methyl-6-octen-1-ol 

Relevant academic research and scientific papers

Tuning stereoselection in Tethered Biginelli condensations. Synthesis of cis- or trans-1-oxo- and 1-iminohexahydropyrrolo[1,2-c]pyrimidines

Stereoselection in tethered Biginelli condensations can be tuned to give either the cis or trans stereoisomer of 1-oxohexahydropyrrolo[1,2- c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).