170716-16-2Relevant academic research and scientific papers
Synthesis of (S)-(-)-Cucurbitine and Conformation of Its Homopeptides
Yamaberi, Yuto,Eto, Ryo,Umeno, Tomohiro,Kato, Takuma,Doi, Mitsunobu,Yokoo, Hidetomo,Oba, Makoto,Tanaka, Masakazu
supporting information, p. 4358 - 4362 (2021/05/26)
A chiral cyclic α,α-disubstituted α-amino acid, (S)-(-)-cucurbitine, which has a pyrrolidine ring with a chiral center at the α-position, was synthesized, and its homopeptides were prepared. (S)-(-)-Cucurbitine homopeptides with a Boc-protecting group formed helical structures with slight control of the helical screw sense to the left-handed form. The state of the pyrrolidine ring in (S)-(-)-cucurbitine was important for the control of the helical structures and helical screw sense of its homopeptides.
Synthesis of optically active 1-(1-phenylethyl)-1H-imidazoles derived from 1-phenylethylamine
Mloston, Grzegorz,Mucha, Paulina,Urbaniak, Katarzyna,Broda, Karolina,Heimgartner, Heinz
body text, p. 232 - 238 (2009/02/07)
The three-component reaction of (R)- or (S)-1-phenylethylamine (6), formaldehyde, and an α-(hydroxyimino) ketone 5, i.e., 3-(hydroxyimino) butan-2-one (5a) or 2-(hydroxyimino)-1,2-diphenylethanone (5b), yields the corresponding enantiomerically pure 1-(1-
A new synthesis of (+)- and (-)-cherylline.
Lebrun, Stephane,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
, p. 1701 - 1706 (2007/10/03)
A new and concise synthesis of enantiopure antipodes of alkaloid cherylline has been devised. The synthetic strategy relies upon the reduction of a diversely and polyprotected diarylenamine bearing a chiral auxiliary. Separation of diastereopure intermediates, concomitant deprotections and intramolecular reductive amination complete the synthesis of the natural (S)-enantiomer and of the unnatural (R)-configured antipode.
Asymmetric synthesis of (+)- and (-)-latifine
Couture, Axel,Deniau, Eric,Grandclaudon, Pierre,Lebrun, Stephane
, p. 1309 - 1316 (2007/10/03)
A concise and novel synthesis of isoquinoline alkaloids (S)-latifine and of its antipode is reported. The key step relies on the stereoselective reduction of an appropriately substituted diarylenamine equipped with a chiral auxiliary followed by Pictet-Sp
N-BH3 ADDUCTS OF TRIALKYL-1,3,5-TRIAZACYCLOHEXANES WITH STABLE STEREOGENIC NITROGEN ATOMS, STEREOCHEMICAL STUDY
Martinez-Aguilera, Luz M. Ruth,Cadenas-Pliego, Gregorio,Contreras, Rosalinda,Flores-Parra, Angelina
, p. 1585 - 1592 (2007/10/02)
The syntheses and stereochemical studies of N-BH3 adducts of trialkyl-1,3,5-triazacyclohexanes are reported.Different reagent ratios were used in order to obtain mono- and di-N-borane adducts.Tri-N-borane adducts were never observed; di-N-borane adducts were formed with triazine 1 and 2 whereas 3 and 4 afforded only the mono-boranes.It appears that low steric strain is an important factor in the syntesis of these compounds.Borane addition produced in all cases ring and nitrogen conformationally stable compounds which were studied by NMR All the reactions were 100percent stereoselective affording one isomer in each reaction.
