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National Chung Hsing University Institutional Repository - NCHUIR > 中興大學 > 期刊論文 >  1,3-bis N-sulfonyl-(1R,2S)-1,3-diphenyl-2-aminopropanol benzene: An excellent ligand for titanium-catalyzed asymmetric AlPh3(THF) additions to aldehydes

Please use this identifier to cite or link to this item: http://nchuir.lib.nchu.edu.tw/handle/309270000/137280

標題: 1,3-bis N-sulfonyl-(1R,2S)-1,3-diphenyl-2-aminopropanol benzene: An excellent ligand for titanium-catalyzed asymmetric AlPh3(THF) additions to aldehydes
作者: Hsieh, S.H.;Chen, C.A.;Chuang, D.W.;Yang, M.C.;Yang, H.T.;Gau, H.M.
關鍵字: asymmetric catalysis;phenyl addition;N-sulfonylated amino alcohol;triphenyl (tetrahydrofuran) aluminum;titanium tetraisopropoxide;beta-amino alcohols;highly enantioselective addition;aromatic-aldehydes;oxovanadium(v) complexes;conjugate addition;carbonyl-compounds;aryl bromides;boronic acids;schiff-bases;reagents
日期: 2008
Issue Date: 2012-12-14 14:29:02 (UTC+8)
關連: Chirality, Volume 20, Issue 8, Page(s) 924-929.
摘要: Asymmetric AlPh3 (THF) additions to a wide variety of aldehydes catalyzed by a titanium catalyst of 20 mol % 1,3-bis[N-sulfonyl-(1R,2S)-1,3-diphenyl-2-aminopropanol] benzene (1) are reported. The catalytic system works excellently for aromatic aldehydes bearing either an electron-donating or an electron-withdrawing substituent on the aromatic ring to afford secondary diaryl alcohols in excellent isolated yields of >= 95% and excellent enantioselectivities of >= 94% ee. The phenyl addition to cinnamaldehyde or 2-furylaldehyde gave corresponding secondary alcohols in 85% and 95% ee, respectively. For aliphatic aldehydes, increasing enantioselectivities of the addition products in terms of increasing steric sizes of aldehydes are observed, and this trend goes from the linear I-pentanal (87% ee), the secondary cyclohexylaldehyde (95% ee) or the 2-methylpropanal (97% ee), to the tertiary 2,2-dimethylpropanal (99% ee).
Relation: Chirality
Appears in Collections:[中興大學] 期刊論文

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