496-47-9

Upstream product

• 127793-67-3 (S)‐7‐(benzyloxy)hept‐1‐en‐4‐ol 
• 1346132-33-9 benzyl-(2R)-2-(2’-oxopropyl) pyrrolidine-1-carboxylate 
• 76470-00-3 methyl 2-(2-oxopropyl)pyrrolidinecarboxylate 
• 56475-88-8 methyl 2-methoxypyrrolidine-1-carboxylate 
• 76460-88-3 N-methoxycarbonyl-2,3-dihydropyrrole 
• 56475-80-0 N-(methoxycarbonyl)pyrrolidine 
• 1202039-23-3 (2R,2'R)-1-[N(1')-(tert-butoxycarbonyl)pyrrolidin-2'-yl]propan-2-ol 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 197229-68-8 N-(benzyloxycarbonyl)-(5R)-5-[(2S)-2,3-dihydroxyprop-1-yl]pyrrolidine 
• 197230-34-5 (R)-2-allyl-(N-benzyloxycarbonyl) pyrrolidine 
• 197229-88-2 (2R-(2S))-1-benzyloxycarbonyl-2-(2,3-epoxypropyl)pyrrolidine 

Relevant academic research and scientific papers

An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline via Keck allylation and CBS reduction

Abstract An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline has been achieved in high optical purity (98% ee) from readily available 1,4-butanediol. The synthesis strategy employs a Keck allylation, CBS reduction, and Wacker oxidation.

Total synthesis of hygrolines and pseudohygrolines

A concise two-step synthesis of all four diastereoisomeric hygrolines ((-)-hygroline (1), (+)-hygroline (2), (-)-pseudohygroline (3), (+)-pseudohygroline (4)) has been developed based on the (-)-sparteine (5)- or (+)-sparteine surrogate 11-mediated enantioselective lithiation of N-Boc pyrrolidine (6), followed by reaction of the chiral anion with (S)- or (R)-propylene oxide. Reduction of the resulting N-Boc amino alcohols furnished hygrolines and pseudohygrolines in 30% to 56% overall yields with dr's > 95:5.

New synthesis of all the four isomers of 2-(2-hydroxypropyl)pyrrolidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement

Both enantiomers of 2-(2-propenyl)pyrrolidine 7 (75-84% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 5, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)pyrrolidines 8 with enantiomeric enhan

Electroorganic Chemistry. 46. A New Carbon-Carbon Bond Forming Reaction at the α-Position of Amines Utilizing Anodic Oxidation as a Key Step

A new carbon-carbon bond forming reaction at the α-position of primary and secondary amines has been exploited.The method involves anodic oxidation of urethanes derived from the primary and secondary amines and subsequent acid-catalyzed reaction of the re