Catalytic asymmetric hydrogenation of β-substituted α,β,γ,δ-unsaturated amino acids

被引:39
作者
Burk, MJ [1 ]
Bedingfield, KM [1 ]
Kiesman, WF [1 ]
Allen, JG [1 ]
机构
[1] Duke Univ, Dept Chem, Paul M Gross Chem Lab, Durham, NC 27706 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(99)00437-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Rh-DuPHOS and Rh-BPE catalyzed hydrogenation of beta-substituted alpha,beta,gamma,delta-unsaturated amino acids establishes two contiguous stereogenic centers simultaneously. Both high regioselectivity and good to excellent enantioselectivity have been demonstrated in this process leading to beta-branched allyl glycine derivatives. Enamide geometry was found to influence stereoselectivity. Studies aimed at defining the scope and limitations of this process are described. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3093 / 3096
页数:4
相关论文
共 11 条
[1]  
BORWN JM, 1982, J CHEM SOC P2, P489
[2]   STRUCTURAL CHARACTERIZATION OF A TRANSIENT INTERMEDIATE IN RHODIUM-CATALYZED ASYMMETRIC HOMOGENEOUS HYDROGENATION [J].
BROWN, JM ;
CHALONER, PA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (08) :344-346
[3]   ASYMMETRIC CATALYTIC SYNTHESIS OF BETA-BRANCHED AMINO-ACIDS VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
GROSS, MF ;
MARTINEZ, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9375-9376
[4]   Asymmetric catalytic routes to chiral building blocks of medicinal interest [J].
Burk, MJ ;
Gross, MF ;
Harper, TGP ;
Kalberg, CS ;
Lee, JR ;
Martinez, JP .
PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :37-44
[5]   A convenient cross-coupling route to alpha,beta,gamma,delta-unsaturated amino acids [J].
Burk, MJ ;
Allen, JG ;
Kiesman, WF ;
Stoffan, KM .
TETRAHEDRON LETTERS, 1997, 38 (08) :1309-1312
[6]   Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems:: Synthesis and application of γ,δ-unsaturated amino acids [J].
Burk, MJ ;
Allen, JG ;
Kiesman, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :657-663
[7]  
BURK MJ, 1985, ASYMMETRIC SYNTHESIS, V5, pCH2
[8]   IDENTIFICATION OF THE ENANTIOSELECTIVE STEP IN THE ASYMMETRIC CATALYTIC-HYDROGENATION OF A PROCHIRAL OLEFIN [J].
CHAN, ASC ;
PLUTH, JJ ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5952-5954
[9]   ASYMMETRIC HYDROGENATION OF METHYL-(Z)-ALPHA-ACETAMIDOCINNAMATE CATALYZED BY (1,2-BIS((PHENYL-ORTHO-ANISOYL)PHOSPHINO)ETHANE)RHODIUM(I) - KINETICS, MECHANISM, AND ORIGIN OF ENANTIOSELECTION [J].
LANDIS, CR ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (06) :1746-1754
[10]   ENANTIOSELECTIVE CATALYSIS .6. THE CATALYTIC-HYDROGENATION OF ALPHA-(ACETYLAMINO)CINNAMIC ACID WITH RHODIUM(I)-BIS(PHOSPHINE) COMPLEXES - ON THE ORIGIN OF THE ENANTIOSELECTION [J].
NAGEL, U ;
RIEGER, B .
ORGANOMETALLICS, 1989, 8 (06) :1534-1538