Some new aspects of the Boyer reaction

被引：19

作者：

Chakraborty, R ^{[1
]}

Franz, V ^{[1
]}

Bez, G ^{[1
]}

Vasadia, D ^{[1
]}

Popuri, C ^{[1
]}

Zhao, CG ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol051442o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction outcome of 2-azidoethanol and aliphatic aldehyde is found to be dependent on the catalyst and the structure of the azido alcohol. Under the catalysis of Cu(II) triflate, the corresponding acetal is obtained. A similar reaction between 2-aryl-2-azidoethanol and aldehyde catalyzed by BF3 yields a mixture of 3-oxazoline and 2-oxazoline. The latter reaction has been used for the preparation of 3-oxazolines in good enantioselectivity.

引用

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页码：4145 / 4148

页数：4

相关论文

共 34 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

[Anonymous], J FOOD SCI

[3] 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

[4] Gallium(III) chloride-catalyzed double insertion of isocyanides into epoxides [J].

Bez, G ;

Zhao, CG .

ORGANIC LETTERS, 2003, 5 (26) :4991-4993

[5] ACID CATALYZED REACTIONS BETWEEN CARBONYL COMPOUNDS AND ORGANIC AZIDES .2. AROMATIC ALDEHYDES [J].

BOYER, JH ;

MORGAN, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (04) :561-562

[6] ACID-CATALYZED REACTIONS OF ALIPHATIC AZIDES [J].

BOYER, JH ;

CANTER, FC ;

HAMER, J ;

PUTNEY, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) :325-327

[7] THE ACID-CATALYZED REACTION OF ALKYL AZIDES UPON CARBONYL COMPOUNDS [J].

BOYER, JH ;

HAMER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (04) :951-954

[8]

CHANG SS, 1968, CHEM IND-LONDON, P1639

[9] Reactions of alkyl azides and ketones as mediated by Lewis acids:: Schmidt and Mannich reactions using azide precursors [J].

Desai, P ;

Schildknegt, K ;

Agrios, KA ;

Mossman, C ;

Milligan, GL ;

Aubé, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7226-7232

[10] Novel synthesis of 3-oxazolines [J].

Favreau, S ;

Lizzani-Cuvelier, L ;

Loiseau, M ;

Duñach, E ;

Fellous, R .

TETRAHEDRON LETTERS, 2000, 41 (50) :9787-9790

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