33398-28-6Relevant academic research and scientific papers
Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration
Luo, Yunfei,Roy, Iain D.,Madec, Amael G. E.,Lam, Hon Wai
supporting information, p. 4186 - 4190 (2014/05/06)
Chiral secondary allylboronates are obtained in high enantioselectivities and 1,6:1,4 ratios by the copper-catalyzed 1,6-boration of electron-deficient dienes with bis(pinacolato)diboron (B2(pin)2). The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol %. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin, in which the key 1,6-boration was performed using only a 0.02 mol % catalyst loading. 1,6-Borations of electron-deficient dienes with bis(pinacolato)diboron using copper catalyst loadings as low as 0.0049 mol % provided chiral allylboronates that, after oxidation, result in allylic alcohols in high enantioselectivities and 1,6:1,4 ratios. The allylboronates can also be used in stereoselective allylations of aldehydes. This process was applied to a concise synthesis of atorvastatin.
A stereospecific phosphonium ylide-salt coupling reaction
Bredenkamp, Martin W.,Lesch, Johanna S.,Malherbe, Johan S.,Molnar, Eva M.,Schneider, David F.
, p. 4199 - 4202 (2007/10/02)
The stereospecific formation of a phosphonium ylide-salt via the stereospecific coupling of an allylic phosphonium ylide with the corresponding phosphonium salt is described.
