- Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration
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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.
- Luo, Yunfei,Roy, Iain D.,Madec, Amael G. E.,Lam, Hon Wai
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supporting information
p. 4186 - 4190
(2014/05/06)
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- AlCl3-NaI(NaBr)-t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives
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(Z)-β-Iodo-propenamides and -β-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and NaI in the presence of t-BuOH in dichlor
- Feray, Laurence,Perfetti, Patricia,Bertrand, Michèle
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experimental part
p. 8733 - 8737
(2009/12/28)
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