Asymmetric Michael addition reactions using a chiral La–Na aminodiolate catalyst
作者： N Prabagaran , G Sundararajan
DOI: 10.1016/S0957-4166(02)00240-9
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摘要: Abstract (R,R)-(+)-2-[Benzyl-(2-hydroxy-2-phenylethyl)amino]-1-phenylethanol 1 is used as a chiral ligand in the synthesis of an optically active lanthanum–sodium amino diol complex LS-1. This heterobimetallic catalyst quite effective asymmetric for various Michael addition reactions, 1H NMR study indicates co-ordination enone to central lanthanum atom The reaction conditions were optimized and adducts obtained high yield with moderate enantiomeric excess under extremely mild conditions.
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G Manickam, G Sundararajan, Lithium bis[(1R,5R)-3-aza-3-benzyl-1,5-diphenylpentan-1,5-diolato]-aluminium — A new heterobimetallic catalyst for Michael addition reactions Tetrahedron. ,vol. 55, pp. 2721- 2736 ,(1999) , 10.1016/S0040-4020(99)00044-7
Hiroaki Sasai, Shigeru Arai, Yoshihiro Tahara, Masakatsu Shibasaki, Catalytic Asymmetric Synthesis of .alpha.-Amino Phosphonates Using Lanthanoid-Potassium-BINOL Complexes Journal of Organic Chemistry. ,vol. 60, pp. 6656- 6657 ,(1995) , 10.1021/JO00126A003
Anke Spannenberg, Markus Oberthür, Henrik Noss, Annegret Tillack, Perdita Arndt, Rhett Kempe, Metal—-Metal “Communication” of Rh or Pd with Nd in Novel Heterobinuclear Complexes Angewandte Chemie International Edition. ,vol. 37, pp. 2079- 2082 ,(1998) , 10.1002/(SICI)1521-3773(19980817)37:15<2079::AID-ANIE2079>3.0.CO;2-Y
Donald J. Cram, G. D. Y. Sogah, Chiral crown complexes catalyse Michael addition reactions to give adducts in high optical yields Journal of the Chemical Society, Chemical Communications. pp. 625- 628 ,(1981) , 10.1039/C39810000625
Shin Aoki, Shigeki Sasaki, Kenji Koga, Simple chiral crown ethers complexed with potassium tert-butoxide as efficient catalysts for asymmetric Michael additions Tetrahedron Letters. ,vol. 30, pp. 7229- 7230 ,(1989) , 10.1016/S0040-4039(01)93942-5
Ken-ichi Yamada, Simon J. Harwood, Harald Gröger, Masakatsu Shibasaki, The First Catalytic Asymmetric Nitro-Mannich-Type Reaction Promoted by a New Heterobimetallic Complex Angewandte Chemie International Edition. ,vol. 38, pp. 3504- 3506 ,(1999) , 10.1002/(SICI)1521-3773(19991203)38:23<3504::AID-ANIE3504>3.0.CO;2-E
Norbert Sträter, William N. Lipscomb, Thomas Klabunde, Bernt Krebs, Two‐Metal Ion Catalysis in Enzymatic Acyl‐ and Phosphoryl‐Transfer Reactions Angewandte Chemie. ,vol. 35, pp. 2024- 2055 ,(1996) , 10.1002/ANIE.199620241
Takahiro Morita, Takayoshi Arai, Hiroaki Sasai, Masakatsu Shibasaki, UTILIZATION OF HETEROBIMETALLIC COMPLEXES AS LEWIS ACIDS Tetrahedron-asymmetry. ,vol. 9, pp. 1445- 1450 ,(1998) , 10.1016/S0957-4166(98)00124-4
Hiroaki Sasai, Takeyuki Suzuki, Noriie Itoh, Koichi Tanaka, Tadamasa Date, Kimio Okamura, Masakatsu Shibasaki, Catalytic asymmetric nitroaldol reaction using optically active rare earth BINOL complexes : investigation of the catalyst structure Journal of the American Chemical Society. ,vol. 115, pp. 10372- 10373 ,(1993) , 10.1021/JA00075A068
Bryant E. Rossiter, Nicole M. Swingle, Asymmetric conjugate addition Chemical Reviews. ,vol. 92, pp. 771- 806 ,(1992) , 10.1021/CR00013A002