A new approach to the stereoselective carbodiazenylation of olefins by macrocyclization

被引:16
作者
Heinrich, Markus R. [1 ]
Blank, Olga [1 ]
Wetzel, Alexander [1 ]
机构
[1] Tech Univ Munich, D-85747 Garching, Germany
关键词
azo compounds; cyclizations; diastereoselectivity; macrocycles; radicals;
D O I
10.1055/s-2006-951556
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reduction of bisaryldiazonium salts in the presence of olefins leads to macrocyclic azo compounds. Chiral auxiliaries incorporated in the bisaryldiazonium salt allow the stereochemical control of the newly formed carbon center.
引用
收藏
页码:3352 / 3354
页数:3
相关论文
共 19 条
[1]  
ALADEL I, 1976, B SOC CHIM FR II-CH, P934
[2]   Carbodiazenylation of olefins by radical iodine transfer and addition to arenediazonium salts [J].
Blank, Olga ;
Heinrich, Markus R. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4331-4334
[3]   Asymmetric catalysis .108. Copper catalysts with optically active ligands in the enantioselective Meerwein arylation of activated olefins [J].
Brunner, H ;
Bluchel, C ;
Doyle, MP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 541 (1-2) :89-95
[4]   Total synthesis of hyacinthacine A1 and 3-epi-hyacinthacine A1 [J].
Chabaud, L ;
Landais, Y ;
Renaud, P .
ORGANIC LETTERS, 2005, 7 (13) :2587-2590
[5]   Stereoselective intermolecular carboazidation of chiral allylsilanes [J].
Chabaud, L ;
Landais, Y ;
Renaud, P .
ORGANIC LETTERS, 2002, 4 (24) :4257-4260
[6]  
CITTERIO A, 1980, SYNTHESIS-STUTTGART, P291
[7]   STERIC, POLAR, AND RESONANCE EFFECTS IN REACTIVITY AND REGIOSELECTIVITY OF ARYL RADICAL-ADDITION TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
CITTERIO, A ;
MINISCI, F ;
VISMARA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :81-88
[8]   STERIC AND POLAR EFFECTS IN FREE-RADICAL REACTIONS - AN UNUSUAL TYPE OF AZOCOUPLING BY FREE-RADICAL DECOMPOSITION OF DIAZONIUM SALTS [J].
CITTERIO, A ;
MINISCI, F ;
ALBINATI, A ;
BRUCKNER, S .
TETRAHEDRON LETTERS, 1980, 21 (30) :2909-2910
[9]  
COHEN SG, 1970, J BIOL CHEM, V245, P5718
[10]   Reductive carbodiazenylation of nonactivated olefins via aryl diazonium salts [J].
Heinrich, Markus R. ;
Blank, Olga ;
Woelfel, Sabrina .
ORGANIC LETTERS, 2006, 8 (15) :3323-3325