221493-43-2

Upstream product

• 760930-39-0 (S)-3-amino-1-benzyloxy-7-methyl-6-octene 
• 221493-07-8 (R)-benzyloxy-7-methyloct-6-en-3-ol 
• 87894-26-6 (R)-(-)-3-hydroxy-7-methyl-6-octenoic acid methyl ester 
• 93041-02-2 (3R)-1,2-dihydroxy-7-methyloct-6-ene 
• 100-39-0 benzyl bromide 

Downstream Products

• 316831-30-8 N-[1-Amino-1-[(S)-2-(2-benzyloxy-ethyl)-5-hydroxy-pyrrolidin-1-yl]-meth-(E)-ylidene]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide 

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).