58648-11-6Relevant articles and documents
FACTORS CONTROLLING THE DIASTEREOFACE SELECTIVITY IN THE COMPLEMENTARY ASYMMETRIC ALKYLATION OF α-ALKYL β-KETO ESTERS
Tomioka, Kiyoshi,Ando, Kaori,Takemasa, Yutaka,Koga, Kenji
, p. 5677 - 5680 (1984)
Complementary asymmetric alkylation reaction of the lithioenamine derived from 2-methoxycarbonylcyclohexanone and (S)-valine tert-butyl ester was examined by employing the various electron pair donating additives in a toluene solvent, in order to clarify
Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis
Chen, Shuming,Han, Feng,Houk, K. N.,Ivlev, Sergei,Meggers, Eric,Xie, Xiulan,Ye, Chen-Xi
supporting information, p. 13552 - 13556 (2020/06/05)
A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 percent yield and with up to >99.5 percent ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.
Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: Synthesis of cyclic amines with a tertiary fluorine at C3
Anxionnat, Bruno,Robert, Benoit,George, Pascal,Ricci, Gino,Perrin, Marc-Antoine,Gomez Pardo, Domingo,Cossy, Janine
experimental part, p. 6087 - 6099 (2012/09/11)
As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of
Studies on diastereoselective reduction of cyclic β-ketoesters with boron hydrides. Part 4: The reductive profile of functionalized cyclohexanone derivatives
Fraga, Carlos A.M.,Teixeira, Lis Helena P.,Menezes, Carla Maria De S.,Sant'Anna, Carlos Mauricio R.,Ramos, Maria Da Concei??o K.V.,De Aquino Neto, Francisco R.,Barreiro, Eliezer J.
, p. 2745 - 2755 (2007/10/03)
Reduction of 2-allyl-2-carboalkoxycyclohexanones (3d-f), 2-propyl-2-carboethoxycyclohexanone (3g) and 2-benzyl-2- carboethoxycyclohexanone (3h) with boron hydrides in the presence and absence of several chelating agents were studied. Molecular modeling studies using semiempirical PM3 method were performed in order to find a suitable explanation of the diastereoselection of ketone carbonyl faces during the reductive process, which yielded trans-2-allyl-2-carboethoxycyclohexanol (6e) and cis-2-allyl-2-carboethoxycyclohexanol (7e) in good diastereomeric excess by using inexpensive sodium and tetrabutylammonium borohydrides.
