116782-26-4Relevant academic research and scientific papers
Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to α-chiral aldehydes: Formal synthesis of all eight L-hexoses
Man, Soo Bong,Kong, Jong Rock,Krische, Michael J.
supporting information; experimental part, p. 4133 - 4135 (2009/05/27)
(Chemical Equation Presented) Hydrogenative coupling of acetylene to α-chiral aldehydes 1a-4a using enantiomeric rhodium catalysts ligated by (S)-MeO-BIPHEP and (R)-MeO-BIPHEP delivers the diastereomeric products of carbonyl-(Z)-buladienylation 1b-4b and 1c-4c, respectively, with good to excellent levels of catalyst directed diastereofacial selectivity. Diastereomeric L-glyceraldehyde acetonide adducts 1b and 1c were converted to the four isomeric enoates 6b, 8b, 6c, and 8c, representing a formal synthesis of all eight L-hexoses.
Diastereoselective addition of organomanganese compounds to α-alkoxysubstituted propanals
Kasatkin, A. N.,Biktimirov, R. Kh.,Podlipchuk, I. P.,Sultanmuratova, V. R.,Tolstikov, G. A.
, p. 161 - 165 (2007/10/02)
Reactions of organomanganese compounds R1MnI (R1 = Ph, 4-MeC6H4, Me, Bu, n-C7H15, BuCC, PhCC),prepared from R1Li and MnI2 in Et2O, with aldehydes MeCH(OR2)CHO (R2 = CH2Ph, CH2OMe, CH2OCH2Ph) afford threo-alcohols MeCH(OR2)CH(OH)R1 with high diastereoselec
Erythro-Directive Reduction of α-Substituted Alkanones by Means of Hydrosilanes in Acidic Media
Fujita, Makoto,Hiyama, Tamejiro
, p. 5415 - 5421 (2007/10/02)
Hydrosilane reduced α-oxy and α-amino ketones and β-keto acid derivatives in trifluoroacetic acid to afford the corresponding erythro alcohols with high diastereoselectivity.The reaction proceeded without racemization at the carbon α to the carbonyl group.The erythro-directive reduction was explained in terms of the proton-bridged Cram cyclic model and successfully applied to the synthesis of physiologically important amino alcohols such as l-ephedrine, l-methoxamine, and erythro-2-methyl-3-piperidino-1-phenylpropanol.
ZnBr2-MEDIATED HIGHLY DIASTEREOSELECTIVE ADDITION OF GRIGNARD REAGENTS TO α-BENZYLOXY ALDEHYDES
Asami, Masatoshi,Kimura, Rieko
, p. 1221 - 1222 (2007/10/02)
α-Benzyloxy aldehydes reacted with Grignard reagents in the presence of ZnBr2 to afford vicinal syn-diol derivatives with high diastereoselectivity.
