Highly regioselective radical cyclizations of allenamides

被引：84

作者：

Shen, LC ^{[1
]}

Hsung, RP ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol047572z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first radical cyclizations of allenamides are described. These reactions are highly regioselective for the central carbon of the allenic moiety, leading to an efficient preparation of nitrogen heterocycles such as isoquinolines, and carbocycles such as indane and naphthalene derivatives. The exo-cyclization mode could also be achieved in some cases, leading to the synthesis of isoindoles. The feasibility of a tandem radical cyclization using allenamide is also established.

引用

收藏

页码：775 / 778

页数：4

相关论文

共 52 条

[1] Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes [J].

Achmatowicz, M ;

Hegedus, LS .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2229-2234

[2]

Allan GM, 2002, SYNLETT, P1431

[3] New regio and stereoselective intermolecular Pauson-Khand reactions of allenamides [J].

Anorbe, L ;

Poblador, A ;

Domínguez, G ;

Pérez-Castells, J .

TETRAHEDRON LETTERS, 2004, 45 (23) :4441-4444

[4] Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine:: synthesis of N-allenylsulfenimides [J].

Armstrong, A ;

Cooke, RS ;

Shanahan, SE .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (18) :3142-3143

[5] Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl Sulfides with tert-butoxycarbonyl azide.: Access to N-allenylsulfenimides [J].

Bacci, JP ;

Greenman, KL ;

Van Vranken, DL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4955-4958

[6] Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides [J].

Berry, CR ;

Hsung, RP .

TETRAHEDRON, 2004, 60 (35) :7629-7636

[7]

Berry CR, 2003, SYNLETT, P791

[8] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[9] Highly diastereoselective indium-mediated allylation of chiral hydrazones [J].

Cook, GR ;

Maity, BC ;

Kargbo, R .

ORGANIC LETTERS, 2004, 6 (11) :1741-1743

[10]

COOK GR, 2004, ORG LETT, V6, P2842

← 1 2 3 4 5 6 →