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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 19期

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

页码：3281 / 3284

页数：4

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

← 1 2 →