39201-99-5Relevant academic research and scientific papers
Chiral ruthenium-catalyzed hydrogenation of β-keto sulfoxides
De Paule, Sebastien Duprat,Piombo, Laurent,Ratovelomanana-Vidal, Virginie,Greek, Christine,Genet, Jean-Pierre
, p. 1535 - 1537 (2007/10/03)
The diastereoselective catalytic hydrogenation of β-keto sulfoxides in the presence of ruthenium complexes was studied. Optically pure β-keto sulfoxides were hydrogenated in the presence of achiral catalysts leading to moderate yields and stereoselectivities. Using chiral ruthenium catalysts such as [(R)-MeO-BIPHEPRuBr2] and [(S)-MeO-BIPHEPRuBr2], the hydrogenation proceeded in good yields with very high diastereoselectivity. Chirality at the secondary centre of the β-hydroxy sulfoxides produced was controlled by the catalysts.
Stereoselective Reductions of 2-Keto Sulfoxides with Hydrides
Carreno, M. Carmen,Ruano, Jose L. Garcia,Martin, Ana M.,Pedregal, Concepcion,Rodriguez, Jesus H.,et al.
, p. 2120 - 2128 (2007/10/02)
The results of reductions of some acyclic 2-keto sulfoxides (ArC(O)CH2S(O)R; Ar=Ph, 2-Py, 4-Py, and R=Me, p-Tol) and flexible and rigid 2-sulfinylcyclohexanone diastereomers with various metal hydrides are reported.The configurational assignment and confo
REDUCTION OF β-HYDROXYSULFOXIDES: APPLICATION TO THE SYNTHESIS OF OPTICALLY ACTIVE EPOXIDES
Solladie, Guy,Demailly, Gilles,Greck, Christine
, p. 435 - 438 (2007/10/02)
β-hydroxysulfoxides of opposite stereochemistry can be prepared in very high diastereoisomeric excesses (90 to 95 percent) by reduction of β-ketosulfoxides with DIBAL or DIBAL/ZnCl2.A very efficient method to transform these reduction products into optically active epoxides is also described.
Highly Diastereoselective Reduction of Chiral β-Ketosulphoxides under Chelation Control: Application to the Synthesis of (R)-(+)-n-Hexadecano-1,5-lactone
Kosugi, Hiroshi,Konta, Hiroshi,Uda, Hisashi
, p. 211 - 213 (2007/10/02)
The presence of zinc chloride in the reduction of chiral β-ketosulphoxides with di-isobutylaluminium hydride effects high 1,3-asymmetric induction to give β-hydroxysulphoxides; this method can be successfully applied to the synthesis of optically pure 1,4
INFLUENCE DE LA NATURE DU LIGAND AROMATIQUE SUR L'INDUCTION ASYMETRIQUE OBSERVEE LORS DE L'ADDITION D'ARYLMETHYLSULFOXYDES SUR DES CARBONYLES
Demailly, Gilles,Greck, Christine,Solladie, Guy
, p. 4113 - 4116 (2007/10/02)
The presence of an orthopyridyl substituent instead of a p-Tolyl on a chiral sulfoxide group increased drastically the asymmetric induction observed during the addition of arylmethylsulfoxide on carbonyl compounds.
Diastereoselektive Addition of (R)-Methyl p-Tolyl Sulfoxide to Benzaldehyde
Braun, Manfred,Hild, Wilhelm
, p. 413 - 414 (2007/10/02)
(R)-Methyl-p-tolyl-sulfoxid (1a) laesst sich nach Umwandlung ins Zinkreagens 1c diastereoselektiv an Benzaldehyd zu 2a/2b addieren.Entschwefelung des durch Umkristallisation rein gewonnenen Ueberschussdiastereomeren 2a liefert das (S)-Carbinol 3.
