1447464-04-1Relevant articles and documents
Stereoselective Access to Azetidine-Based α-Amino Acids and Applications to Small Peptide Synthesis
Didier, Dorian,Joseph, Emanuel,Ni?l, Benedikt,Reiners, Felix
, p. 8533 - 8537 (2020)
Non-natural azetidine-based amino acids (Aze) present interesting features in protein engineering. A simple organometallic route toward unsaturated carboxylic acid precursors is presented. Subsequent metal-catalyzed asymmetric reduction allowed for the sy
Synthesis of Simple 3,3-Diarylazetidines from N-Boc-3-arylazetidinols Using Friedel-Crafts Arylation Conditions
Das, Madhurima,Weissenfluh, Amber,Ly, Nam,Trudell, Mark L.
, p. 8209 - 8213 (2020/07/25)
A synthesis of 3,3-diarylazetidines from N-Boc-3-aryl-3-azetidinols using Friedel-Crafts arylation conditions with AlCl3 is described. A series of substituted diarylazetidines were readily prepared and isolated as the oxalate salts in high yield and high
Oxidative Deconstruction of Azetidinols to α-Amino Ketones
Allen, Lewis A. T.,Natho, Philipp,Parsons, Philip J.,Raclea, Robert-Cristian,White, Andrew J. P.
, p. 9375 - 9385 (2020/08/14)
A silver-mediated synthesis of α-amino ketones via the oxidative deconstruction of azetidinols has been developed using a readily scalable protocol with isolated yields up to 80percent. The azetidinols are easily synthesized in one step and can act as protecting groups for these pharmaceutically relevant synthons. Furthermore, mechanistic insights are presented and these data have revealed that the transformation is likely to proceed through the β-scission of an alkoxy radical, followed by oxidation and C-N cleavage of the resulting α-amido radical.
A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl–Alkyl Cross-Coupling Reactions
Greb, Andreas,Poh, Jian-Siang,Greed, Stephanie,Battilocchio, Claudio,Pasau, Patrick,Blakemore, David C.,Ley, Steven V.
, p. 16602 - 16605 (2017/12/13)
Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon–carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2)?C(sp3) cross-coupling processes, with excellent functional-group tolerance.
3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters
Thaxton, Amber,Izenwasser, Sari,Wade, Dean,Stevens, Edwin D.,Mobley, David L.,Jaber, Vivian,Lomenzo, Stacey A.,Trudell, Mark L.
supporting information, p. 4404 - 4407 (2013/07/25)
A series of 3-aryl-3-arylmethoxy-azetidines were synthesized and evaluated for binding affinities at dopamine and serotonin transporters. The 3-aryl-3-arylmethoxyazetidines were generally SERT selective with the dichloro substituted congener 7c (Ki = 1.0 nM) and the tetrachloro substituted derivative 7i (Ki = 1.3 nM) possessing low nanomolar affinity for the SERT. The 3-(3,4-dichlorophenyl-3-phenylmethoxyazetidine (7g) exhibited moderate affinity at both DAT and SERT transporters and suggests that substitution of the aryl rings can be used to tune the mononamine transporter affinity.
