1294444-86-2Relevant academic research and scientific papers
Asymmetric syntheses of APTO and AETD: The β-amino acid fragments within microsclerodermins C, D, and e
Davies, Stephen G.,Fletcher, Ai M.,Foster, Emma M.,Lee, James A.,Roberts, Paul M.,Thomson, James E.
, p. 2500 - 2510 (2013/05/22)
Efficient asymmetric syntheses of APTO and AETD, the highly functionalized β-amino acid fragments within microsclerodermins C, D, and E, are reported. The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to tert-butyl (E,E)-7-(triisopropylsilyloxy)hepta-2,4-dienoate and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine, diastereoselective dihydroxylation of a 2,3-syn-γ,δ-unsaturated-α-hydroxy-β- amino ester derivative under Donohoe conditions, and a Julia-Kocienski olefination were used as the key steps.
Highly diastereoselective and stereodivergent dihydroxylations of acyclic allylic amines: Application to the asymmetric synthesis of 3,6-dideoxy-3-amino- l-talose
Csatayova, Kristina,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Wilson, David L.
supporting information; experimental part, p. 2606 - 2609 (2011/07/08)
Aminohydroxylation of tert-butyl sorbate [tert-butyl (E,E)-hexa-2,4- dienoate] using enantiopure lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and (-)-camphorsulfonyloxaziridine gives tert-butyl (R,R,R,E)-2-hydroxy-3-[N- benzyl-N-(α-methylbenzyl)amino]hex-4-enoate in >99:1 dr. Subsequent dihydroxylation under Upjohn conditions (OsO4/NMO) gives tert-butyl (2R,3R,4S,5S,αR)-2,4,5-trihydroxy-3-[N-benzyl-N-(α-methylbenzyl) amino]hexanoate (in 95:5 dr) while dihydroxylation under Donohoe conditions (OsO4/TMEDA) proceeds with antipodal diastereofacial selectivity to give the (R,R,R,R,R)-diastereoisomer (in 95:5 dr). The amino triols resulting from these dihydroxylation reactions are useful for further elaboration, as demonstrated by the asymmetric synthesis of 3,6-dideoxy-3-amino-l-talose.
