54867-10-6Relevant academic research and scientific papers
Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids
Davies, Jacob,Janssen-Müller, Daniel,Zimin, Dmitry P.,Day, Craig S.,Yanagi, Tomoyuki,Elfert, Jonas,Martin, Ruben
supporting information, p. 4949 - 4954 (2021/04/07)
A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.
Solvent-enhanced diastereo- and regioselectivity in the pd IIcatalyzed synthesis of six- and eight-membered heterocycles via cis-aminopalladation
Balazs, Arpad,Hetenyi, Anasztazia,Szakonyi, Zsolt,Sillanpaeae, Reijo,Fueloep, Ferenc
scheme or table, p. 7376 - 7381 (2010/03/24)
The PdII-catalyzed intramolecular oxidative cyclization of tosyl-protected cis- and frans-N-allyl-2-aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane-fused pyrimidin-4-ones and l,5-diazocin-6-ones were developed.
Synthesis and microbial transformation of β-amino nitriles
Winkler, Margit,Martínková, Ludmila,Knall, Astrid C.,Krahulec, Stefan,Klempier, Norbert
, p. 4249 - 4260 (2007/10/03)
Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce β-amino amides and acids from β-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitriles gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work.
EXPERIMENTAL STUDIES OF THE ANOMERIC EFFECT. PART 2 RING INVERSION AND NITROGEN INVERSION EQUILIBRIA IN CIS-DECAHYDROQUINAZOLINES
Booth, Harold,Khedhair, Khedhair A.,Al-Shirayda, Hatif A. R. Y.
, p. 1465 - 1476 (2007/10/02)
The positions of conformational equilibria due to the double ring inversion in cis-decahydroquinazoline (7-->//07-->8 1.08 kcal mol-1; -ΔG09-->10 1.10 kcal mol-1) for the conformation which would allow the lone pairs on N(1) and N(3) to lie on the hindered 'inside' face of the molecules.However, the values of 3J(CHNH) coupling constants for both cis-decahydro-3-methylquinazoline (10) and cis (4aH, 8aH) cis (2H, 8aH)-decahydro-2,3-dimethylquinazoline (14) show that the N-inversion equilibrium at N(1) prefers the conformation in which N(1)-H is 'inside' (axial), and N(1)-lone pair equatorial, thus demonstrating the ability of the anomeric effect to outweigh steric repulsions.
