Novel imidazolination reaction of alkenes provides an easy access to new α,β-differentiated 1,2-vicinal diamines

被引:28
作者
Pei, W [1 ]
Timmons, C [1 ]
Xu, X [1 ]
Wei, HX [1 ]
Li, GG [1 ]
机构
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
关键词
D O I
10.1039/b305149h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha,beta-Differentiated 1,2-vicinal diamines have been efficiently synthesized by using new electrophilic imidazolination reaction of alkenes. The hydrolysis of imidazolines was performed by treatment with 6 M HCl in THF at 70 degreesC without epimerization. Eight examples were examined to give good to excellent yields (87-96%).
引用
收藏
页码:2919 / 2921
页数:3
相关论文
共 34 条
[1]  
Alexakis A, 1998, SYNLETT, P873
[2]   Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives [J].
Bernardi, L ;
Gothelf, AS ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2583-2591
[3]   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
[4]   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
[5]   A simplified synthesis of (+/-)-1,2-diphenyl-1,2-diaminoethane (1) from benzaldehyde and ammonia. Revision of the structures of the long-known intermediates ''hydrobenzamide'' and ''amarine'' [J].
Corey, EJ ;
Kuhnle, FNM .
TETRAHEDRON LETTERS, 1997, 38 (50) :8631-8634
[6]   VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS [J].
COREY, EJ ;
KIM, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4976-4977
[7]   Synthesis of phosphoramides for the Lewis base-catalyzed allylation and aldol addition reactions [J].
Denmark, SE ;
Su, YP ;
Nishigaichi, Y ;
Coe, DM ;
Wong, KT ;
Winter, SBD ;
Choi, JY .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1958-1967
[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]   An efficient asymmetric route to 2,3-diaminobutanoic acids [J].
Han, HS ;
Yoon, J ;
Janda, KD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :2045-2048