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|標題:||Study on the synthesis of new chiral derivatives of squaric acid and their application in asymmetric catalytic borane reduction of prochiral aryl ketones||作者:||Lu, S.M.
|關鍵字:||chiral squaric acid amidoalcohols;chiral oxazaborolidine;asymmetric;catalysis;reduction of aryl ketones;aromatic ketones;enantioselective reduction;ligands||Project:||Acta Chimica Sinica||期刊/報告no：:||Acta Chimica Sinica, Volume 59, Issue 4, Page(s) 587-593.||摘要:||
Eleven new chiral squaric acid amidoalcohols bave been synthesized by reaction of alkyl amines or thiols with 3 - butoxy - [(1'S, 2'R) - (2' - hydroxy - 1', 2' - diphenylethyl) amino] - 3 - cyclobutene - 1, 2 - dione,which is prepared by the reaction of (1R, 2S) - 2 - amino - 1, 2 - diphenylalcohol with dibutyl squrate, The in situ formed chiral oxazaborolidines have been used in the enantioselective borane reduction of prochiral ketones to afford the alcohol products in a range 88% similar to 98% yield and 42% similar to 81% enantiomeric excesses, respectively. All of the new compounds are confirmed by IR, H-1 NMR, MS and element analysis, in which compound 4b is also confirmed by X - ray analysis.
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