Cu(I)-catalyzed cycloguanidination of olefins

被引:63
作者
Zhao, Baoguo [1 ]
Du, Haifeng [1 ]
Shi, Yian [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
关键词
D O I
10.1021/ol702974s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes a novel cycloguanidination process using CuCl as catalyst and diaziridinimines as the nitrogen source. A variety of conjugated dienes, trienes, and terminal olefins can be effectively diaminated under mild reaction conditions, For dienes and trienes, the reaction occurs at the terminal double bond with high regioselectivity.
引用
收藏
页码:1087 / 1090
页数:4
相关论文
共 65 条
[1]  
ARANDA VG, 1974, SYNTHESIS-STUTTGART, P504
[2]   Oxaziridine rearrangements in asymmetric synthesis [J].
Aube, J .
CHEMICAL SOCIETY REVIEWS, 1997, 26 (04) :269-277
[3]   NEW COPPER(I)-CATALYZED REACTIONS OF OXAZIRIDINES - STEREOCHEMICAL CONTROL OF PRODUCT DISTRIBUTION [J].
AUBE, J ;
PENG, X ;
WANG, YG ;
TAKUSAGAWA, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5466-5467
[4]  
BACKVALL JE, 1978, TETRAHEDRON LETT, P163
[5]   THE FIRST ENANTIOSPECIFIC PALLADIUM-CATALYZED CYCLOADDITION OF AZIRIDINES AND HETEROCUMULENES - NOVEL SYNTHESIS OF CHIRAL 5-MEMBERED RING HETEROCYCLES [J].
BAEG, JO ;
BENSIMON, C ;
ALPER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4700-4701
[6]   SYNTHESIS OF CYCLIC N-CYANOGUANIDINES [J].
BALTZER, CM ;
MCCARTY, CG .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :155-156
[7]   Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].
Bar, GLJ ;
Lloyd-Jones, GC ;
Booker-Milburn, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309
[8]  
BARLUENGA J, 1979, SYNTHESIS-STUTTGART, P962
[9]   A NEW METHOD FOR 1,2-DIAMINATION OF ALKENES USING CYCLOPENTADIENYLNITROSYLCOBALT DIMER-NO-LIALH4 [J].
BECKER, PN ;
WHITE, MA ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) :5676-5677
[10]   Natural guanidine derivatives [J].
Berlinck, RGS ;
Kossuga, MH .
NATURAL PRODUCT REPORTS, 2005, 22 (04) :516-550