請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/68508
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
期刊/報告no:: 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).
URI: http://hdl.handle.net/11455/68508
ISSN: 0899-0042
文章連結: http://dx.doi.org/10.1002/chir.20572
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