203397-91-5

Upstream product

• 127909-66-4 (2R,3S)-3-Benzyloxymethyl-oxirane-2-carbaldehyde 
• 78469-85-9 (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol 
• 156713-03-0 (2S,3S)-2-Benzyloxymethyl-3-vinyl-oxirane 

Downstream Products

• 315719-02-9 (1R,2R)-N-(1-benzyloxymethyl-2-hydroxy-3-butenyl)-acetamide 
• 315718-97-9 (2R,3S)-2-amino-1-benzyloxypent-4-en-3-ol 
• 315719-06-3 (2R,3R)-2-amino-1-benzyloxypent-4-en-3-ol 
• 330589-23-6 1-((2S,3R)-2-Benzyloxymethyl-3-vinyl-aziridin-1-yl)-ethanone 
• 203398-10-1 (2S,3R)-2-benzyloxymethyl-3-vinyl-aziridine 

Relevant academic research and scientific papers

A regio-and stereodivergent synthesis of vic-amino alcohols

(Matrix presented) A regio-and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by sui

A regio- and stereodivergent route to all isomers of vic-amino alcohols.

Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

Aminolysis of vinyl epoxides as an efficient entry to N-H vinylaziridines

Vinyl epoxides 8a-f 11 and 12 have been prepared from the corresponding epoxy alcohols while 8g was formed by a regioselective epoxidation of the parent diene. Aminolysis of these materials resulted in a regio- and stereoselective nucleophilic opening at C3 in good yields except for the sterically hindered substrates. The trans-oxiranes gave the anti-amino alcohols while the cis derivative 12 gave the syn isomer 17. Cyclization of the anti-amino alcohols was best effected using the Mitsunobu protocol giving the corresponding N-H vinylaziridines in 50-54% yields, while the syn-amino alcohol 17 was transformed into the cis-vinylaziridine 31 with chlorosulfonic acid followed by base treatment in 20% yield. The outcome of these cyclizations seems to indicate that they are controlled by subtle steric effects in the substrate. The N-H vinylaziridine 24 was alkylated with tert-butyl bromoacetate and the product subjected to an aza[2,3]-Wittig rearrangement to give tetrahydropyridine 30 while acetylation of 24 followed by base treatment resulted in an aza-[3,3]-Claisen rearrangement yielding the seven-membered lactam 32.