868696-71-3Relevant academic research and scientific papers
1,2-Sulfone rearrangement in organocatalytic reactions
Quintard, Adrien,Alexakis, Alexandre
experimental part, p. 1407 - 1418 (2011/04/18)
The 1,2-sulfone rearrangement resulting from nucleophilic addition to bis activated vinyl-sulfones has been studied in more detail. Various nucleophiles activated by different types of catalysts (enamine, Broensted base, thiourea) are able to promote such
Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging michael acceptors
Sulzer-Mosse, Sarah,Alexakis, Alexandre,Mareda, Jiri,Bollot, Guillaume,Bernardinelli, Gerald,Filinchuk, Yaroslav
supporting information; experimental part, p. 3204 - 3220 (2009/12/03)
Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99% ee. This novel process provides synthetically useful chiral γ-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail.
Diversity-oriented synthesis towards conceptually new highly modular aminal-pyrrolidine organocatalysts
Quintard, Adrien,Bournaud, Chloee,Alexakis, Alexandre
supporting information; experimental part, p. 7504 - 7507 (2009/08/14)
A study was conducted to demonstrate the synthesis of animal-pyrrolidine derivatives and their applications in various Michael addition reactions. The animal-pyrrolidine organocatalysts were prepared from protected L-prolinal, which was obtained from commercially available Cbz-L-proline. Animal formations with various reoisomers were prepared, while catalysts were synthesized, to study the influence of the different substituents. It was observed that all catalysts were stable after prolonged conservation period. The newly synthesized catalysts were also tested in the reaction of proopinaldehyde with nitrostyrene. It was also observed that all the catalysts lead to full conversion after a short reaction time. The enantioselectivity varied from 49% in diastereoisomeric catalyst, to the best enantioselectivity of 79%, using reoisomer catalysts.
