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

被引：27

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 16期

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

页码：2919 / 2921

页数：3

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
Bernardi, L
Gothelf, AS
Hazell, RG
Jorgensen, KA
[J]. 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
CHONG, AO
OSHIMA, K
SHARPLESS, KB
[J]. 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
COREY, EJ
LEE, DH
SARSHAR, S
[J]. 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''
Corey, EJ
Kuhnle, FNM
[J]. TETRAHEDRON LETTERS, 1997, 38 (50) : 8631 - 8634
[6] VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS
COREY, EJ
KIM, SS
[J]. 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
Denmark, SE
Su, YP
Nishigaichi, Y
Coe, DM
Wong, KT
Winter, SBD
Choi, JY
[J]. 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
Han, HS
Yoon, J
Janda, KD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) : 2045 - 2048

← 1 2 3 4 →