Amine-salt-controlled, catalytic asymmetric conjugate addition of various amines and asymmetric protonation

被引:128
作者
Hamashima, Y [1 ]
Somei, H [1 ]
Shimura, Y [1 ]
Tamura, T [1 ]
Sodeoka, M [1 ]
机构
[1] Tohoku Univ, IMRAM, Sendai, Miyagi 9808577, Japan
关键词
D O I
10.1021/ol0493711
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combined use of chiral Pd complex 2 and amine salt enabled completely regulated release of free nucleophilic amine. Under these conditions, an efficient catalytic asymmetric conjugate addition of various amines was achieved to afford beta-amino acid derivatives in high chemical yields with up to 98% ee. Furthermore, a highly enantioselective protonation in 1,4-addition of amine was also developed.
引用
收藏
页码:1861 / 1864
页数:4
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共 35 条
[1]   Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates [J].
Doi, H ;
Sakai, T ;
Iguchi, M ;
Yamada, K ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2886-2887
[2]   A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations [J].
Emori, E ;
Arai, T ;
Sasai, H ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4043-4044
[3]   Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins [J].
Fadini, L ;
Togni, A .
CHEMICAL COMMUNICATIONS, 2003, (01) :30-31
[4]   Asymmetric titanium-catalysed Michael addition of O-benzylhydroxylamine to alpha,beta-unsaturated carbonyl compounds: Synthesis of beta-amino acid precursors [J].
Falborg, L ;
Jorgensen, KA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (23) :2823-2826
[5]   Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex [J].
Fujii, A ;
Hagiwara, E ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5450-5458
[6]   Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles [J].
Guerin, DJ ;
Miller, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2134-2136
[7]   Enantioselective addition of enol silyl ethers to imines catalyzed by palladium complexes: A novel way to optically active acylalanine derivatives [J].
Hagiwara, E ;
Fujii, A ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2474-2475
[8]   Immobilization and reuse of Pd complexes in ionic liquid:: Efficient catalytic asymmetric fluorination and Michael reactions with β-ketoesters [J].
Hamashima, Y ;
Takano, H ;
Hotta, D ;
Sodeoka, M .
ORGANIC LETTERS, 2003, 5 (18) :3225-3228
[9]   An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes [J].
Hamashima, Y ;
Yagi, K ;
Takano, H ;
Tamás, L ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14530-14531
[10]   Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].
Hamashima, Y ;
Hotta, D ;
Sodeoka, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241