503830-53-3Relevant academic research and scientific papers
A new access to enantiopure syn- and anti-2-methyl-1,3-diol moieties from chiral nonracemic α-bromo α′-sulfinyl ketones promoted by samarium diiodide
Colobert, Francoise,Obringer, Michel,Solladie, Guy
, p. 1455 - 1467 (2006)
syn- and anti-2-Methyl-1,3-diols have been prepared by a two-step sequence that involves a SmI2-promoted stereoselective Reformatsky addition of chiral nonracemic α-bromo α′-sulfinyl ketones to various aldehydes followed by stereoselective redu
A route to "all-cis" 2-methyl-6-substituted piperidin-3-ol alkaloids from syn-(2R,1′S)-2-(1-dibenzylaminomethyl)epoxide: Rapid total synthesis of (+)-deoxocassine
Geant, Pierre-Yves,Martinez, Jean,Salom-Roig, Xavier J.
scheme or table, p. 62 - 65 (2012/02/01)
A general strategy leading to the synthesis of two cis-2-methyl-6- substituted piperidin-3-ols is described. syn-(2R,1′S)-2-(1- Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza-enolate of hydrazones 12a and 12b. Subsequent hydrazone hydrolysis and intramolecular reductive amination afforded the alkaloid (+)-deoxocassine and a new C-6 ethyl analogue of this substance in good yields.
Highly enantioselective access to α-dibenzylamino ketones from chiral nonracemic α-bromo α′-sulfinyl ketones by dynamic kinetic resolution: Synthesis of (2R,1′S)-2-[1-(dibenzylamino)alkyl]oxiranes
Geant, Pierre-Yves,Martinez, Jean,Salom-Roig, Xavier J.
experimental part, p. 1300 - 1309 (2011/04/17)
A novel and efficient synthesis of enantiomerically pure α-dibenzylamino α′-sulfinyl ketones starting from a mixture of both epimers of α-bromo α′-(R)-sulfinyl ketone has been realized through combined in situ substitution-epimerization in a so-called Dynamic Kinetic Resolution (DKR). The scope of the reaction has been examined, and four differently substituted α-(S)-dibenzylamino α′-(R)- sulfinyl ketones were obtained in good yields with excellent diastereoselectivities. The utility of these derivatives was further illustrated with a highly stereoselective synthesis of syn-(2R,1′S)-2-(1- dibenzylaminoalkyl)oxiranes.
Reformatsky-type reaction of chiral nonracemic α-bromo-α′ -sulfinyl ketones with aldehydes. Synthesis of enantiomerically pure 2-methyl-1,3-diol moieties
Obringer, Michel,Colobert, Francoise,Neugnot, Benjamin,Solladie, Guy
, p. 629 - 632 (2007/10/03)
Figure presented Chiral nonracemic α-bromo-α′-sulfinyl ketones were shown to react with aldehydes in the presence of Sml2 in a Reformatsky-type reaction to give the corresponding adduct with excellent syn diastereoselectivity. Further reduction
