A direct catalytic aldol route to protected β-hydroxy-α-amino acids

被引:14
作者
Willis, MC [1 ]
Piccio, VJD [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
关键词
catalysis; amino acids; aldol reaction; Lewis acid;
D O I
10.1055/s-2002-34241
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combination of triethylamine, magnesium(II) perchlorate and bipyridine generates a catalyst system for the efficient combination of ethyl isothiocyanatoacetate and a range of aromatic aldehydes. The products of these reactions are synthetically valuable protected beta-hydroxy alpha-amino acids.
引用
收藏
页码:1625 / 1628
页数:4
相关论文
共 19 条
[1]   An efficient asymmetric synthesis of (2S,3S)- and (2R,3R)-β-hydroxyornithine [J].
DeMong, DE ;
Williams, RM .
TETRAHEDRON LETTERS, 2001, 42 (02) :183-185
[2]   Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones [J].
Evans, DA ;
Downey, CW ;
Shaw, JT ;
Tedrow, JS .
ORGANIC LETTERS, 2002, 4 (07) :1127-1130
[3]   Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones [J].
Evans, DA ;
Tedrow, JS ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :392-393
[4]   Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes [J].
Evans, DA ;
Scheidt, KA ;
Johnston, JN ;
Willis, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4480-4491
[5]   ASYMMETRIC GLYCINE ENOLATE ALDOL REACTIONS - SYNTHESIS OF CYCLOSPORINES UNUSUAL AMINO-ACID, MEBMT [J].
EVANS, DA ;
WEBER, AE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6757-6761
[6]   Catalytic in situ generation of Zn(II)-alkynilides under mild conditions:: A novel C=N addition process utilizing terminal acetylenes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11245-11246
[7]   METALATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .8. 2-THIOXO-OXAZOLIDINES BY CYCLOADDITION OF ALPHA-METALATED ALKYL ISOTHIOCYANATES TO CARBONYL-COMPOUNDS [J].
HOPPE, D ;
FOLLMANN, R .
CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (09) :3047-3061
[8]   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
[9]   POLYOXINS - PYRIMIDINE NUCLEOSIDE PEPTIDE ANTIBIOTICS INHIBITING FUNGAL CELL-WALL BIOSYNTHESIS [J].
ISONO, K ;
SUZUKI, S .
HETEROCYCLES, 1979, 13 :333-351
[10]   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