Direct electrophilic diamination of functionalized alkenes without the use of any metal catalysts

被引：61

作者：

Chen, DJ ^{[1
]}

Timmons, C ^{[1
]}

Wei, HX ^{[1
]}

Li, GG ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 14期

关键词：

D O I：

10.1021/jo030098a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new direct electrophilic diamination reaction of alpha,beta-unsaturated ketones and esters has been established without the use of any metal catalysts. Three types of nitriles (CH3CN, CH3CH2CN, and CH3CH2CH2CN) were employed as nucleophilic nitrogen sources. A new mechanism has also been proposed to explain the resulting regio- and stereoselectivity.

引用

页码：5742 / 5745

页数：4

共 33 条

[1]

BACKVALL JE, 1975, TETRAHEDRON LETT, P2225

[2]

BARLUENGA J, 1981, SYNTHESIS-STUTTGART, P376

[3] beta-silyl diorganozinc compounds - A new class of useful zinc reagents [J].

Berger, S ;

Langer, F ;

Lutz, C ;

Knochel, P ;

Mobley, TA ;

Reddy, CK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1496-1498

[4] SYNTHESIS OF DIOXOBIS(TERT-ALKYLIMIDO)OSMIUM(VIII) AND OXOTRIS(TERT-ALKYLIMIDO)OSMIUM(VIII) COMPLEXES - STEREOSPECIFIC VICINAL DIAMINATION OF OLEFINS [J].

CHONG, AO ;

OSHIMA, K ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) :3420-3426

[5] CONVENIENT ROUTES TO SYMMETRICAL BENZILS AND CHIRAL 1,2-DIARYL-1,2-DIAMINOETHANES, USEFUL CONTROLLERS AND PROBES FOR ENANTIOSELECTIVE SYNTHESIS [J].

COREY, EJ ;

LEE, DH ;

SARSHAR, S .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :3-6

[6] BIFUNCTIONAL CHIRAL AUXILIARIES-3 - SYNTHESIS OF HOMOCHIRAL 1,3-DIOLS VIA ASYMMETRIC ALDOL REACTIONS OF DIALKYLBORON ENOLATES OF 1,3-DIPROPIONYL-TRANS-4,5-DIPHENYL-IMIDAZOLIDIN-2-ONE AND ALDEHYDES [J].

DAVIES, SG ;

MORTLOCK, AA .

TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :1001-1004

[7] A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS [J].

DENG, L ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4320-4323

[8]

Dghaym RD, 2001, ANGEW CHEM INT EDIT, V40, P3228, DOI 10.1002/1521-3773(20010903)40:17<3228::AID-ANIE3228>3.0.CO

[9]

2-Q

[10] Erythro-selective aldol-type reaction of N-sulfonylaldimines with methyl isocyanoacetate catalyzed by gold(I) [J].

Hayashi, T ;

Kishi, E ;

Soloshonok, VA ;

Uozumi, Y .

TETRAHEDRON LETTERS, 1996, 37 (28) :4969-4972

← 1 2 3 4 →