Copper(II) acetate promoted intramolecular diamination of unactivated olefins

被引:186
作者
Zabawa, TP [1 ]
Kasi, D [1 ]
Chemler, SR [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/ja053335v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise method for the synthesis of cyclic sulfamides and vicinal diamines is presented. This method is enabled by Cu(OAc)2 and demonstrates a new transformation for this metal. Both five- and six-membered vicinal diamine-containing heterocycles have been synthesized in good to excellent yields, and substrate-based asymmetric induction has been achieved. This is the first reported example of intramolecular diamination of olefins. Copyright © 2005 American Chemical Society.
引用
收藏
页码:11250 / 11251
页数:2
相关论文
共 24 条
[1]  
BACKVALL JE, 1978, TETRAHEDRON LETT, P163
[2]   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
[3]  
BARLUENGA J, 1979, SYNTHESIS-STUTTGART, P962
[4]   A TRANSITION-METAL-BASED METHOD FOR 1,2-DIAMINATION OF ALKENES - SYNTHESIS OF COBALT DINITROSOALKANES FROM ALKENES, NITRIC-OXIDE, AND (ETA-5-CYCLOPENTADIENYL)NITROSYLCOBALT DIMER AND THEIR REDUCTION TO PRIMARY VICINAL DIAMINES [J].
BECKER, PN ;
BERGMAN, RG .
ORGANOMETALLICS, 1983, 2 (07) :787-796
[5]   Ritter-type reactions of N-chlorosaccharin:: A method for the electrophilic diamination of alkenes [J].
Booker-Milburn, KI ;
Guly, DJ ;
Cox, B ;
Procopiou, PA .
ORGANIC LETTERS, 2003, 5 (18) :3313-3315
[6]   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
[7]  
Cotton F., 1999, ADV INORGANIC CHEM
[8]   Ring-closing metathesis strategies to cyclic sulfamide peptidomimetics [J].
Dougherty, JM ;
Probst, DA ;
Robinson, RE ;
Moore, JD ;
Klein, TA ;
Snelgrove, KA ;
Hanson, PR .
TETRAHEDRON, 2000, 56 (50) :9781-9790
[9]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[10]   Highly selective synthesis of heterosubstituted aromatic sulfamides [J].
Hof, F ;
Iovine, PM ;
Johnson, DW ;
Rebek, J .
ORGANIC LETTERS, 2001, 3 (26) :4247-4249