4063-69-8Relevant academic research and scientific papers
Enantioselective synthesis of O-methoxycarbonyl cyanohydrins: Chiral building blocks generated by bifunctional catalysis with BINOLAM-AlCl
Baeza, Alejandro,Casas, Jesús,Nájera, Carmen,Sansano, José M.,Saá, José M.
, p. 1949 - 1958 (2006)
(R)- or (S)-BINOLAM-AlCl, generated in situ, work as bifunctional catalysts in promoting the enantioselective cyanoalkoxycarbonylation of aldehydes. The reaction is wide in scope and the mechanistic evidence gathered suggests the intervention of an indirect process involving enantioselective hydrocyanation by HCN, followed by O-alkoxycarbonylation. The resultant O-alkoxycarbonyl cyanohydrins are shown to be important chiral building blocks for synthesis. Chemoselective hydrolysis can thus be directed either to provide enantioenriched β-hydroxy esters, or acids, or instead to give O-methoxycarbonyl β-hydroxy acids, esters, or amides. In addition, the enantiopure cyanocarbonates can be converted into β-amino alcohols by reduction with lithiumaluminium hydride. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
