93406-80-5Relevant academic research and scientific papers
Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor
Ka?mierczak, Marcin,Kubicki, Maciej,Koroniak, Henryk
, p. 3844 - 3852 (2018/07/31)
We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).
Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins
Raza, Abdul Rauf,Saddiqa, Aisha,?akmak, Osman
, p. 951 - 957 (2015/11/16)
A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.
Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids
Saddiqa, Aisha,Raza, Abdul R.,Black, David Stc.,Kumar, Naresh
, p. 736 - 743 (2014/06/09)
The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.
Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines-development of a phosphite-driven cyclodehydration
Huy, Peter H.,Westphal, Julia C.,Koskinen, Ari M.P.
supporting information, p. 369 - 383 (2014/03/21)
A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.
Synthesis of a new class of bis(thiourea)hydrazide pseudopeptides as potential inhibitors of β-sheet aggregation
Klein, Jan J.,Hecht, Stefan
supporting information; experimental part, p. 330 - 333 (2012/02/04)
The modular synthesis of a novel pseudopeptide scaffold based on a bis(thiourea)hydrazide motif is reported. This compound class is designed to display "amphifinity", i.e. association with a peptide strand on one but not the other face of the scaffold, and hence could potentially inhibit β-sheet aggregation.
Asymmetric transfer hydrogenation using amino acid derivatives; Further studies and a mechanistic proposal
Yim, Aveline S. Y.,Wills, Martin
, p. 7994 - 8004 (2007/10/03)
A series of investigations into the use of amino acid derivatives for the asymmetric catalysis of the transfer hydrogenation of ketones are presented. Based on the results observed, a mechanistic suggestion for the origin of the enantioselective induction
New organometallic approach to derivatives of α-substituted statines from N,N-dibenzylaminoaldehydes
Le Carrer-Le Goff, Nicolas,Audin, Patrick,Paris, Jo?lle,Cazes, Bernard
, p. 6325 - 6328 (2007/10/03)
α-Substituted statines derivatives were synthesized via the zinc-mediated allylation of N,N-dibenzyl α-aminoaldehydes followed by ozonolysis of the intermediate homoallylic alcohols.
(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids
Camps, Pelayo,Perez, Francesc,Soldevilla, Nuria,Borrego, Miguel A.
, p. 493 - 509 (2007/10/03)
rac-α-Amino acids (rac-1a-d) were formally deracemized by a four-step reaction sequence: (a) protection of the amino function as the phthalimido derivative; (b) acyl chloride formation; (c) diastereoselective reaction with the chiral auxiliaries (R)- or (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2- pyrrolidinone, (R)- or (S)-3; and (d) acid hydrolysis to deprotect both the ester and phthalimido functions. Diastereoselectivities of the intermediate esters 4 were good (82-96% d.e.), except for the case of 4b (41% d.e.), the precursor of valine. The main diastereoisomer of esters 4 was (αR,3S)- or (αS,3R)-, except for 4d: in this case, working at -78°C, the (αR,3R)- diastereoisomer was the main product, which epimerizes easily at the α- position when at room temperature. Acid hydrolysis of esters 4 directly gave the deprotected α-amino acids, with little or no epimerization at the α- position of the α-amino acid and complete recovery of the chiral auxiliary. Only (αR,3R)-4d on acid hydrolysis partially epimerized at the α-position. Moreover, some α-amino acids and their N,N-dibenzyl derivatives were obtained by dynamic kinetic resolution of diastereoisomeric mixtures of α- bromo esters 5 derived from the chiral auxiliaries (R)- or (S)-3 during reaction with dibenzylamine.
Stereoselective synthesis of the four stereoisomers of 4-(N,N- dibenzylamino)-2,2-dimethyl-3-hydroxypentanenitrile
Moriarty, Robert M.,Tao, Anping,Tuladhar, Sudersan M.
, p. 3227 - 3234 (2007/10/03)
The title compounds 1(a,b) and 1(c,d) were synthesized by (i) non- chelation controlled sodium borohydride reduction of their corresponding α- N,N-dibenzylaminoketones and (ii) the Aldol-type condensation of optically pure N,N-dibenzylaminoaldehydes with the lithium derivative of isobutyronitrile, respectively. Attempted inversion of configurations of these secondary alcohols using the Moriarty method yielded 4 -chloro-3 -N,N- dibenzylaminonitrile via an aziridinium ion intermediate instead of the expected inverted alcohols.
