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
Berger, S
Langer, F
Lutz, C
Knochel, P
Mobley, TA
Reddy, CK
[J]. 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
CHONG, AO
OSHIMA, K
SHARPLESS, KB
[J]. 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
COREY, EJ
LEE, DH
SARSHAR, S
[J]. 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
DAVIES, SG
MORTLOCK, AA
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (10) : 1001 - 1004
[7] A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS
DENG, L
JACOBSEN, EN
[J]. 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)
Hayashi, T
Kishi, E
Soloshonok, VA
Uozumi, Y
[J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4969 - 4972

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