82495-70-3Relevant academic research and scientific papers
Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols
Beccalli, Egle Maria,Giofrè, Sabrina,Lo Presti, Leonardo,Molteni, Letizia,Nava, Donatella
supporting information, p. 21723 - 21727 (2021/09/08)
An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza-)alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent-iodine compounds have been compared. I
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.
Stereoselective Synthesis of 1,2-trans-Diamines Using the Three-Component Borono-Mannich Condensation – Reaction Scope and Mechanistic Insights
Norsikian, Stéphanie,Beretta, Margaux,Cannillo, Alexandre,Auvray, Marie,Martin, Amélie,Retailleau, Pascal,Iorga, Bogdan I.,Beau, Jean-Marie
, p. 1940 - 1951 (2017/04/21)
The Petasis borono-Mannich (PBM) process with easily accessible N-protected α-amino aldehydes produces 1,2-trans-diamines diastereoselectively with an enantiomeric excess up to 98 %. The protecting group on the nitrogen atom had a decisive influence on bo
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
Synthesis of enantioenriched 1,2-trans-diamines using the borono-Mannich reaction with N-protected α-amino aldehydes
Norsikian, Stéphanie,Beretta, Margaux,Cannillo, Alexandre,Martin, Amélie,Retailleau, Pascal,Beau, Jean-Marie
supporting information, p. 9991 - 9994 (2015/06/22)
The three-component Petasis borono-Mannich reaction starting with easily accessible N-protected α-amino aldehydes produces efficiently and diastereoselectively 1,2-trans-diamines with an enantiomeric excess of up to 98%.
Enantioselective addition of ArTi(OiPr)3 to aldehydes catalyzed by a titanium complex of an N-sulfonylated amino alcohol
Chang, Shih-Ju,Zhou, Shuangliu,Gau, Han-Mou
, p. 9368 - 9373 (2015/02/19)
Asymmetric additions of ArTi(OiPr)3 to aldehydes catalyzed by a titanium catalyst of N-sulfonylated amino alcohols were reported, and results showed that the chiral N-sulfonylated amino alcohol with two stereogenic centers could catalyze the asymmetric addition of ArTi(OiPr)3 to aldehydes to afford desired secondary alcohols in good yields with good to excellent enantioselectivities of up to 95% ee.
Two rearrangement pathways in the geminal acylation of 2-methoxyoxazolidines leading to substituted 1,4-oxazines
Moulins, Jonathan R.,Hughes, Jeremy A.,Doyle, Lauren E.,Cameron, T. Stanley,Burnell, D. Jean
supporting information, p. 1325 - 1332 (2015/03/04)
Lewis acid-mediated geminal acylation of 2-methoxyoxazolidines with five- or six-membered acyloins followed by heterocyclization afforded 1,4-oxazines fused to cyclopentenone or cyclohexenone rings. Overall yields ranged from 30 to 73%. The position of the carbonyl group in the products depended on whether or not water was present during the ringexpanding acyl migration step. The route lacking water during the acyl migration step was best conducted in one pot. The addition of water effected cleavage of a silyloxy group in the intermediate during the initial Mukaiyama aldol reaction prior to the acyl migration.
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 (2013/10/21)
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.
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
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
