کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1347383 980307 2008 12 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Asymmetric catalysis of carbon–carbon bond forming reactions using amino acid-derived C1-symmetrical salen ligands
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Asymmetric catalysis of carbon–carbon bond forming reactions using amino acid-derived C1-symmetrical salen ligands
چکیده انگلیسی

Four amino acids (alanine, valine, phenylalanine and phenylglycine) have been converted into C1-symmetrical salen ligands and complexed to titanium, vanadium, copper and cobalt. The resulting complexes have been used as asymmetric catalysts for asymmetric cyanohydrin synthesis, asymmetric Strecker reactions, asymmetric synthesis of α-methyl amino acids and asymmetric Darzens condensations. Satisfactory levels of asymmetric induction were obtained from reactions in which the (salen)metal complex acts as a chiral Lewis acid, but low levels of asymmetric induction were obtained from reactions carried out under solid–liquid phase-transfer conditions.

Figure optionsDownload as PowerPoint slide

(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-1,2-diaminopropaneC33H50N2O2[α]D20=+173.0 (c 0.1, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-3-phenyl-1,2-diaminopropaneC39H54N2O2[α]D20=+63.5 (c 0.052, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

(1R)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-1-phenyl-1,2-diaminoethaneC38H53N2O2[α]D20=-27.2 (c 0.25, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-3-methyl-1,2-diaminobutaneC35H54N2O2[α]D20=+84.0 (c 0.1, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

(2S)-[N,N′-Bis-(2′-hydroxy-4′-methoxy benzylidene)]-1,2-diaminopropaneC19H22N2O4[α]D20=+425.0 (c 0.04, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

(2S)-[N,N′-Bis-(2′-hydroxy-4′-methoxy benzylidene)]-3-phenyl-1,2-diaminopropaneC25H26N2O4[α]D20=+67.0 (c 0.06, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

(1R)-[N,N′-Bis-(2′-hydroxy-4′-methoxy benzylidene)]-1-phenyl-1,2-diaminoethaneC24H24N2O4[α]D20=-60.0 (c 0.06, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

(2S)-[N,N′-Bis-(2′-hydroxy-4′-methoxy benzylidene)]-3-methyl-1,2-diaminobutaneC21H26N2O4[α]D20=+78.6 (c 0.5, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-1,2-diaminopropaneC17H18N2O2[α]D20=+332.0 (c 0.05, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-3-phenyl-1,2-diaminopropaneC23H22N2O2[α]D20=+88.0 (c 0.05, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-3-methyl-1,2-diaminobutaneC19H22N2O2[α]D20=+250.0 (c 0.03, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-1,2-diaminopropanato] titaniumIV chlorideC33H48N2O2TiCl2[α]D20=+800.0 (c 0.003, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-3-phenyl-1,2-diaminopropanato] titaniumIV chlorideC39H52N2O2TiCl2[α]D20=-266.7 (c 0.006, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

[(1R)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-1-phenyl-1,2-diaminoethanato] titaniumIV chlorideC38H50N2O2TiCl2[α]D20=+1300.0 (c 0.004, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

[(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-3-methyl-1,2-diaminobutanato] titaniumIV chlorideC35H52N2O2TiCl2[α]D20=-240.0 (c 0.005, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-1,2-diaminopropanato] vanadiumV chlorideC33H48N2O3VCl[α]D20=+1050.0 (c 0.002, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-3-phenyl-1,2-diaminopropanato] vanadiumV chlorideC39H52N2O3VCl[α]D20=-690.0 (c 0.02, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

[(1R)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-1-phenyl-1,2-diaminoethanato] vanadiumV chlorideC38H50N2O3VCl[α]D20=+320.0 (c 0.02, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

[(2S)-[N,N′-Bis-(2′-hydroxy-3′,5′-di-tert-butyl benzylidene)]-3-methyl-1,2-diaminobutanato] vanadiumV chlorideC35H52N2O3VCl[α]D20=-3600.0 (c 0.0033, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-1,2-diaminopropanato] copperIIC17H16N2O2Cu[α]D20=-140.0 (c 0.02, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-3-phenyl-1,2-diaminopropanato] copperIIC23H20N2O2Cu[α]D20=-320.0 (c 0.01, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

[(1)-[N,N′-Bis-(2′-hydroxybenzylidene)]-1-phenyl-1,2-diaminoethanato] copperIIC22H18N2O2Cu[α]D20=-400.0 (c 0.01, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

[(1)-[N,N′-Bis-(2′-hydroxybenzylidene)]-1-phenyl-1,2-diaminoethaneC22H20N2O2[α]D20=+88.0 (c 0.05, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

[(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-3-methyl-1,2-diaminobutanato] copperIIC19H22N2O2Cu[α]D20=-160.0 (c 0.01, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-1,2-diaminopropanato] cobaltIIC17H16N2O2Co[α]D20=-1180.0 (c 0.02, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-3-phenyl-1,2-diaminopropanato] cobaltIIC23H20N2O2Co[α]D20=-720.0 (c 0.01, CHCl3).Prepared from (S)-phenylalanineAbsolute configuration: (2S)

[(1)-[N,N′-Bis-(2′-hydroxybenzylidene)]-1-phenyl-1,2-diaminoethanato] cobaltIIC22H18N2O2Co[α]D20=+640.0 (c 0.01, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

[(2S)-[N,N′-Bis-(2′-hydroxybenzylidene)]-3-methyl-1,2-diaminobutanato] cobaltIIC19H22N2O2Co[α]D20=-707.7 (c 0.013, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxy-4′-methoxybenzylidene)]-1,2-diaminopropanato] cobaltIIC19H20N2O4Co[α]D20=-560.0 (c 0.01, CHCl3)Prepared from (S)-alanineAbsolute configuration: (2S)

[(2S)-[N,N′-Bis-(2′-hydroxy-4′-methoxybenzylidene)]-3-phenyl-1,2-diaminopropanato] cobaltIIC25H24N2O4Co[α]D20=-1500.0 (c 0.02, CHCl3)Prepared from (S)-phenylalanineAbsolute configuration: (2S)

[(1R)-[N,N′-Bis-(2′-hydroxy-4′-methoxybenzylidene)]-1-phenyl-1,2-diaminoethanato] cobaltIIC24H22N2O4Co[α]D20=+440.0 (c 0.01, CHCl3)Prepared from (R)-phenylglycineAbsolute configuration: (1R)

[(2S)-[N,N′-Bis-(2′-hydroxy-4′-methoxybenzylidene)]-3-methyl-1,2-diaminobutanato] cobaltIIC19H24N2O4Co[α]D20=-160.0 (c 0.01, CHCl3)Prepared from (S)-valineAbsolute configuration: (2S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 24, 12 December 2008, Pages 2804–2815
نویسندگان
, , ,