Titanium catalysis in the Ugi reaction of α-amino acids with aromatic aldehydes

被引:51
作者
Godet, T
Bonvin, Y
Vincent, G
Merle, D
Thozet, A
Ciufolini, MA
机构
[1] Lab Synth & Methodol Organ, CNRS, UMR 5181, F-69622 Villeurbanne, France
[2] Univ Lyon 1, Ctr Commun Diffractometrie, F-69622 Villeurbanne, France
[3] Ecole Super Chim Phys & Elect, F-69622 Villeurbanne, France
关键词
D O I
10.1021/ol048850x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ugi reaction between an (S)-alpha-amino acid, an aromatic aldehyde, and an isonitrile proceeds best under catalysis by TiCl4 in MeOH. The sense of diastereoinduction is (S,S).
引用
收藏
页码:3281 / 3284
页数:4
相关论文
共 12 条
[1]   Synthesis of chiral 1,1'-iminodicarboxylic acid derivatives from alpha-amino acids, aldehydes, isocyanides, and alcohols by the diastereoselective five-center four-component reaction [J].
Demharter, A ;
Horl, W ;
Herdtweck, E ;
Ugi, I .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :173-175
[2]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[3]  
2-U
[4]   Synthesis of novel chiral ligands from amino acids by the Ugi reaction [J].
Dyker, G ;
Breitenstein, K ;
Henkel, G .
TETRAHEDRON-ASYMMETRY, 2002, 13 (17) :1929-1936
[5]   Amino acid derivatives by multicomponent reactions [J].
Dyker, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (16) :1700-1702
[6]   Oxazolidine ring opening and lsomerization to (E)-imines.: Asymmetric synthesis of aryl-α-fluoroalkyl amino alcohols [J].
Gosselin, F ;
Roy, A ;
O'Shea, PD ;
Chen, CY ;
Volante, RP .
ORGANIC LETTERS, 2004, 6 (04) :641-644
[7]   Novel α-amino amidine synthesis via scandium(III) triflate mediated 3CC Ugi condensation reaction [J].
Keung, W ;
Bakir, F ;
Patron, AP ;
Rogers, D ;
Priest, CD ;
Darmohusodo, V .
TETRAHEDRON LETTERS, 2004, 45 (04) :733-737
[8]   A facile synthesis of N-carbamoylmethyl-α-aminobutyrolactones by the Ugi multicomponent condensation reaction [J].
Park, SJ ;
Keum, G ;
Kang, SB ;
Koh, HY ;
Kim, Y ;
Lee, DH .
TETRAHEDRON LETTERS, 1998, 39 (39) :7109-7112
[9]   Multicomponent reactions are accelerated in water [J].
Pirrung, MC ;
Das Sarma, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :444-445
[10]   AMIDOALKYLATION OF AROMATICS WITH GLYOXYLIC ACID-GAMMA-LACTAM ADDUCTS - 2-PYRROLIDINONE, PYROGLUTAMIC ACID AMIDE AND ESTER [J].
ROTH, E ;
ALTMAN, J ;
KAPON, M ;
BENISHAI, D .
TETRAHEDRON, 1995, 51 (03) :801-810