An Efficient Oxidative Conversion of Aldehydes into 2-Substituted 2-Oxazolines Using 1,3-Diiodo-5,5-dimethylhydantoin

被引：19

作者：

Takahashi, Shogo ^{[1
]}

Togo, Hideo ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Inage Ku, Chiba 2638522, Japan

来源：

SYNTHESIS-STUTTGART | 2009年 / 14期

关键词：

2-aryl-2-oxazoline; 2-alkyl-2-oxazoline; 1,3-diiodo-5,5-dimethylhydantoin; aldehyde; 2-aminoethanol; chiral oxazoline; CHIRAL NITRIDOMANGANESE COMPLEX; POT DIRECT SYNTHESIS; CARBOXYLIC-ACIDS; MOLECULAR-IODINE; OXAZOLINES; OLEFINS; 2-IMIDAZOLINES; THIAZOLINES; VERSATILE; ALCOHOLS;

D O I：

10.1055/s-0029-1216843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions.

引用

页码：2329 / 2332

页数：4

共 57 条

[1]

APPLE R, 1975, ANGEW CHM INT ED ENG, V14, P801

[2] One-step conversion of aldehydes to oxazolines and 5,6-dihydro-4H-1,3-oxazines using 1,2- and 1,3-azido alcohols [J].

Badiang, JG ;

Aube, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2484-2487

[3] Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions [J].

Bandgar, BP ;

Pandit, SS .

TETRAHEDRON LETTERS, 2003, 44 (11) :2331-2333

[4] SYNTHESIS AND SOLUTION STRUCTURE OF MICROBIAL SIDEROPHORES [J].

BERGERON, RJ .

CHEMICAL REVIEWS, 1984, 84 (06) :587-602

[5] Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation [J].

Bhor, S ;

Anilkumar, G ;

Tse, MK ;

Klawonn, M ;

Dobler, C ;

Bitterlich, B ;

Grotevendt, A ;

Beller, M .

ORGANIC LETTERS, 2005, 7 (16) :3393-3396

[6]

Boyd G.V., 1984, COMPREHENSIVE HET 4B, V6, P178

[7] Catalytic applications of chiral organoselenium compounds in asymmetric synthesis [J].

Braga, Antonio L. ;

Ludtke, Diogo S. ;

Vargas, Fabricio ;

Braga, Rodolpho C. .

SYNLETT, 2006, (10) :1453-1466

[8] Some new aspects of the Boyer reaction [J].

Chakraborty, R ;

Franz, V ;

Bez, G ;

Vasadia, D ;

Popuri, C ;

Zhao, CG .

ORGANIC LETTERS, 2005, 7 (19) :4145-4148

[9] A versatile synthesis of 2,4-substituted oxazoles [J].

Chudasama, Vijay ;

Wilden, Jonathan D. .

CHEMICAL COMMUNICATIONS, 2008, (32) :3768-3770

[10] A simple synthesis of 2-substituted oxazolines and oxazines [J].

Cwik, A ;

Hell, Z ;

Hegedüs, A ;

Finta, Z ;

Horváth, Z .

TETRAHEDRON LETTERS, 2002, 43 (22) :3985-3987

← 1 2 3 4 5 6 →