129646-78-2Relevant academic research and scientific papers
Chemoenzymatic dynamic kinetic resolution of allylic alcohols: A highly enantioselective route to acyloin acetates
Bogar, Krisztian,Vidal, Pilar Hoyos,Alcantara Leon, Andres R.,Baeckvall, Jan-E.
, p. 3401 - 3404 (2007)
Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to
Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ
Jiang, Shan-Shan,Gu, Bo-Qi,Zhu, Ming-Yu,Yu, Xingxin,Deng, Wei-Ping
, p. 1187 - 1191 (2015/02/19)
Chiral α-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic α-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer
Remote stereocontrol mediated by a sulfinyl group: Synthesis of allylic alcohols via chemoselective and diastereoselective reduction of γ-methylene δ-ketosulfoxides
Ruano, Jose L. Garcia,Fernandez-Ibanez, M. Angeles,Fernandez-Salas, Jose A.,Maestro, M. Carmen,Marquez-Lopez, Pablo,Rodriguez-Fernandez, M. Mercedes
experimental part, p. 1200 - 1204 (2009/07/18)
The efficiency of the sulfinyl group as a remote controller of the chemoselectivity and diastereoselectivity of the reduction of α,β-unsaturated α-[2-(p-tolylsulfinyl)phenyl] substituted ketones 1 has been demonstrated in reactions carried out under NaBH
Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp.
Burgess, Kevin,Jennings, Lee D.
, p. 6129 - 6139 (2007/10/02)
Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of β-hydroxy-α-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of γ-hydroxy-α,β-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.
