Axially chiral directly β,β-linked bisporphyrins:: Synthesis and stereostructure

被引:55
作者
Bringmann, Gerhard [1 ]
Ruedenauer, Stefan [1 ]
Goetz, Daniel C. G. [1 ]
Gulder, Tobias A. M. [1 ]
Reichert, Matthias [1 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
关键词
SEMIEMPIRICAL METHODS; LINKED DIPORPHYRIN; PORPHYRIN DIMERS; DENSITY; CATALYSTS; RECOGNITION; CYCLIZATION; ALDEHYDES; EXCHANGE; LIGANDS;
D O I
10.1021/ol061812o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel type of "superbiaryl", the first porphyrin dimers with an intrinsically chiral structure, has been prepared. The atropo-enantiomers were configurationally assigned by HPLC-CD combined with quantum chemical CD calculations.
引用
收藏
页码:4743 / 4746
页数:4
相关论文
共 36 条
[1]   A NEW MIXING OF HARTREE-FOCK AND LOCAL DENSITY-FUNCTIONAL THEORIES [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (02) :1372-1377
[2]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[3]   DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].
BECKE, AD .
PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100
[4]   Ancisheynine, the first N,C-coupled naphthylisoquinoline alkaloid:: Total synthesis and stereochemical analysis [J].
Bringmann, G ;
Guider, T ;
Reichert, M ;
Meyer, F .
ORGANIC LETTERS, 2006, 8 (06) :1037-1040
[5]   The 'lactone method':: enantioselective preparation of novel P,N-biaryl ligands and their use in the synthesis of the biarylic alkaloids, ancistrotanzanine B and ancistroealaine A [J].
Bringmann, G ;
Pfeifer, RM ;
Schreiber, P ;
Hartner, K ;
Schraut, M ;
Breuning, M .
TETRAHEDRON, 2004, 60 (20) :4349-4360
[6]   Stereochemistry of isoplagiochin C, a macrocyclic bisbibenzyl from liverworts [J].
Bringmann, G ;
Mühlbacher, J ;
Reichert, M ;
Dreyer, M ;
Kolz, J ;
Speicher, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9283-9290
[7]   Novel concepts in directed biaryl synthesis.: Part 107.: Synthesis of enantiopure axially chiral C3-symmetric tripodal ligands and their application as catalysts in the asymmetric addition of dialkylzinc to aldehydes [J].
Bringmann, G ;
Pfeifer, RM ;
Rummey, C ;
Hartner, K ;
Breuning, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6859-6863
[8]   Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [J].
Bringmann, G ;
Breuning, M .
TETRAHEDRON-ASYMMETRY, 1998, 9 (04) :667-679
[9]  
Bringmann G., 1998, Natural Products Analysis Eds, P195
[10]  
BRINGMANN G, 2005, ANGEW CHEM, V44, P5518