100132-60-3Relevant academic research and scientific papers
An improved, convenient procedure for reduction of amino acids to aminoalcohols: Use of NaBH4-H2so4
Abiko, Atsushi,Masamune, Satoru
, p. 5517 - 5518 (1992)
The use of NaBH4-H2SO4, For the reduction of α-amino acids to the corresponding aminoalcohols offers definite advantages: i) operational simplicity, ii) ease of scaling up the reaction without risking explosion, and iii) use of the inexpensive reagents.
An efficient synthetic approach for N-C bond formation from (S)-amino acids: An easy access to cis-2,5-disubstituted chiral piperazines
Manna, Sudipta Kumar,Panda, Gautam
, p. 18332 - 18338 (2013)
An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N-C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.
Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines
Craig, Donald,Spreadbury, Samuel R. J.,White, Andrew J. P.
supporting information, p. 9803 - 9806 (2020/09/16)
Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.
Synthesis of Enantiopure PZM21: A Biased Agonist of the Mu-Opioid Receptor
Perrey, David,Zhang, Dehui,Nguyen, Thuy,Carroll, F. Ivy,Ko, Mei-Chuan,Zhang, Yanan
, p. 4006 - 4012 (2018/07/30)
PZM21 (1) was recently reported as a biased agonist of the mu-opioid receptor (MOR) with improved antinociceptive effects and reduced side effects compared with traditional opioid-based analgesics. The original synthesis of PZM21 with the desired (S,S) configuration required the separation of a diastereomeric mixture in the final step by using chiral HPLC. A concise synthesis of 1 has now been developed in the enantiomeric pure form starting with commercially available l-alanine and proceeding via a chiral aziridine as a key intermediate. The final product was obtained as the (S,S) diastereomer in seven steps in 22.5 % yield from l-alanine. This synthetic strategy could be readily applied to the development of PZM21 analogues at the thiophenyl position.
Lewis acid mediated intramolecular C-O bond formation of alkanol-epoxide leading to substituted morpholine and 1,4-oxazepane derivatives: Total synthesis of (±)-Viloxazine
Ghosh, Priya,Deka, Manash J.,Saikia, Anil K.
, p. 690 - 698 (2016/01/15)
Substituted morpholines have been efficiently synthesised in good yields from nitrogen tethered alkanol-epoxide mediated by boron trifluoride etherate. The methodology has been used for the total synthesis of (±)-viloxazine.
Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion
Balaji, Pandur Venkatesan,Chandrasekaran, Srinivasan
supporting information, p. 70 - 72 (2014/01/06)
An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang
Palladium-catalyzed atom transfer radical cyclization of unactivated alkyl iodide
Liu, Hui,Qiao, Zongjun,Jiang, Xuefeng
supporting information; experimental part, p. 7274 - 7277 (2012/09/25)
A palladium-catalyzed atom transfer cyclization of unactivated alkyl iodide has been developed. A radical chain mechanism has been proposed for this transformation, which might not involve an alkylpalladium intermediate.
Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes
Sequeira, Fatima C.,Chemler, Sherry R.
supporting information, p. 4482 - 4485 (2012/10/29)
A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines we
Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines
Samanta, Krishnananda,Panda, Gautam
supporting information; experimental part, p. 189 - 197 (2011/10/08)
An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3·OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright
Diversity-oriented synthesis based on the dppp-catalyzed mixed double-michael reactions of electron-deficient acetylenes and β-amino alcohols
Fan, Yi Chiao,Kwon, Ohyun
scheme or table, p. 3802 - 3825 (2011/06/24)
In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)- propane (DPPP)-catalyzed mixed double-Michael reactions of β-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions for the preparation of five-membered-ring heterocycles, we prepared 60 distinct oxazolidines from five β-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived β-amino alcohols.
