Catalytic enantioselective aldol additions of α-isothiocyanato imides to α-ketoesters

被引:39
作者
Vecchione, Matthew K. [1 ]
Li, Le [1 ]
Seidel, Daniel [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
关键词
AMINO ACID-DERIVATIVES; QUATERNARY AMMONIUM-SALTS; ASYMMETRIC-SYNTHESIS; CINCHONA ALKALOIDS; NONADJACENT STEREOCENTERS; CONJUGATE ADDITION; EFFICIENT APPROACH; CYCLIC-PEPTIDES; BOND DONORS; SCHIFF-BASE;
D O I
10.1039/c0cc00556h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A readily available bifunctional thiourea catalyst promotes aldol additions of alpha-isothiocyanato imides to alpha-ketoesters under mild reaction conditions to form beta-hydroxy-alpha-amino acid derivatives with high levels of enantioselectivity.
引用
收藏
页码:4604 / 4606
页数:3
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共 72 条
[21]   Enantioselective organocatalysis [J].
Gaunt, Matthew J. ;
Johansson, Carin C. C. ;
McNally, Andy ;
Vo, Ngoc T. .
DRUG DISCOVERY TODAY, 2007, 12 (1-2) :8-27
[22]   Organocatalytic asymmetric formal [3+2]cycloaddition reaction of isocyanoesters to nitroolefins leading to highly optically active dihydropyrroles [J].
Guo, Chang ;
Xue, Meng-Xia ;
Zhu, Ming-Kui ;
Gong, Liu-Zhu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3414-3417
[23]   VANCOMYCIN - STRUCTURE AND TRANSFORMATION TO CDP-I [J].
HARRIS, CM ;
KOPECKA, H ;
HARRIS, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6915-6922
[24]   Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl) serine as potential in vivo precursors of fluorinated norepinephrines [J].
Herbert, B ;
Kim, IH ;
Kirk, KL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4892-4897
[25]   Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst [J].
Horikawa, M ;
Busch-Petersen, J ;
Corey, EJ .
TETRAHEDRON LETTERS, 1999, 40 (20) :3843-3846
[26]   Synthesis of β-hydroxy-β-(fluoronitrophenyl)alanines:: Vital components in the assembly of biologically active cyclic peptides [J].
Hutton, CA .
ORGANIC LETTERS, 1999, 1 (02) :295-297
[27]   STUDIES ON POLYOXINS, ANTIFUNGAL ANTIBIOTICS .13. STRUCTURE OF POLYOXINS [J].
ISONO, K ;
ASAHI, K ;
SUZUKI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (26) :7490-+
[28]   CATALYTIC ASYMMETRIC ALDOL REACTION - REACTION OF ALDEHYDES WITH ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].
ITO, Y ;
SAWAMURA, M ;
HAYASHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6405-6406
[29]   Direct Organocatalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imides to α-Ketoesters under Low Ligand Loading: A Doubly Stereocontrolled Approach to Cyclic Thiocarbamates Bearing Chiral Quaternary Stereocenters [J].
Jiang, Xianxing ;
Zhang, Gen ;
Fu, Dan ;
Cao, Yiming ;
Shen, Fangfang ;
Wang, Rui .
ORGANIC LETTERS, 2010, 12 (07) :1544-1547
[30]   A convenient synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-threo-(3,4-dihydroxyphenyl)serine using Sharpless asymmetric aminohydroxylation [J].
Kim, IH ;
Kirk, KL .
TETRAHEDRON LETTERS, 2001, 42 (48) :8401-8403