Application of Enantiopure 1-(Aminoalkyl)naphthols and 2-(Aminoalkyl) phenols in the Enantioselective Addition of Organozinc to ,-Unsaturated Carbonyl Compounds

Synthetic Communications

Volumn 39, Issue 17, 2009, Pages 3184-3190

  Cimarelli, Cristina ^a   Fratoni, Davide ^a   Palmieri, Gianni ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

1 (Aminoalkyl)naphthols; 2 (aminoalkyl)phenols; Chalcones; Enantioselective conjugated addition

Indexed keywords

CARBONYL DERIVATIVE; CHALCONE DERIVATIVE; NICKEL; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 68749109504     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902737148     Document Type: Article

References (20)

1. Kretchmer, R. A. 1,4-Addition of organometallic reagents to α,β-unsaturated ketones in the presence of (-)-sparteine. J. Org. Chem. 1972, 37, 2744-2747.
2. Langer, W.; Seebach, D. Enantioselective 1,4-additions of organometallic compounds to conjugated systems in a chiral 1,4-bis(dimethylamino)-23- dimethoxybutane medium. Helv. Chim. Acta 1979, 62, 1710-1722.
3. Leyendecker, F.; Jesser, F.; Laucher, D. Ligand effects in enantioface-differentiating 1,4-addition to 1,3-diphenyl-2-propen-1-one. Tetrahedron Lett. 1983, 24, 3513-3516.
4. Alexakis, A.; Mutti, S.; Normant, F. New chiral ligand for the asymmetric conjugate addition of organocopper reagents to enones. J. Am. Chem. Soc. 1991, 113, 6332-6334.
5. Krause, N.; Hoffmann-Röder, A. Recent advances in catalytic enantioselective Michael additions. Synthesis 2001, 2, 171-196.
6. Wakimoto, I.; Tomioka, Y.; Kawanami, Y. Catalytic enantioselective conjugate addition of diethylzinc to chalcones using chiral amino alcohol-nickel complexes. Tetrahedron 2002, 58, 8095-8097.
7. Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation. J. Org. Chem. 2001, 66, 4759-4765.
8. Palmieri, G. Synthesis of enantiopure 2-hydroxybenzylamines by stereoselective reduction of 2-imidoylphenols: Application in the catalytic enantioselective addition of diethylzinc to aldehydes. Eur. J. Org. Chem. 1999, 805-811.
9. Palmieri, G. A practical o-hydroxybenzylamines promoted enantioselective addition of dialkylzincs to aldehydes with asymmetric amplification. Tetrahedron: Asymmetry 2000, 11, 3361-3373.
10. Soai, K.; Hayasaka, T.; Ugajin, S. Asymmetric synthesis of optically active b-substituted ketones by highly enantioselective catalytic conjugate addition of dialkylzinc reagents to enones using a catalyst system of nickel(II)-chiral ligand-achiral ligand in acetonitrile/toluene. J. Chem. Soc., Chem. Commun. 1989, 516-517.
11. Ohkuma, T.; Sandoval, C. A.; Srinivasan, R.; Lin, Q.; Wei, Y.; Muniz, K.; Noyori, R. Asymmetric hydrogenation of tert-alkyl ketones. J. Am. Chem. Soc. 2005, 127, 8288-8289.
12. Hajra, A.; Yoshikai, N.; Nakamura, E. Aminohydroxyphosphine ligand for the copper-catalyzed enantioselective conjugate addition of organozinc reagents. Org. Lett. 2006, 8, 4153-4156.
13. Leitereg, T. J.; Cram, D. J. Studies in stereochemistry, XXXVII: Open-chain models for 1,3-asymmetric induction in stereospecific addition polymerization. J. Am. Chem. Soc. 1968, 90, 4011-4018.
14. Ito, K.; Eno, S.; Saito, B.; Katsuki, T. Enantioselective conjugate addition of diethylzinc to acyclic enones using a copper phosphino-phenol complex as catalyst. Tetrahedron Lett. 2005, 46, 3981-3986.
15. Huttenloch, O.; Spieler, J.; Waldmann, H. Chiral bicyclic phosphoramidites - A new class of ligands for asymmetric catalysis. Chem. Europ. J. 2001, 7, 671-675.
16. Shi, M.; Wang, C.-J.; Zhang, W. Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system. Chem. Europ. J. 2004, 10 (21), 5507-5516.
17. Soai, K.; Okudo, M.; Okamoto, M. Enantioselective conjugate addition of diethylzinc to enones using chiral β-aminoalcohol as chiral catalyst or ligand. Tetrahedron Lett. 1991, 32 (1), 95-96.
18. Takahashi, Y.; Yamamoto, Y.; Katagiri, K.; Danjo, H.; Yamaguchi, K.; Imamoto, T. P-Chiral o-phosphinophenol as a P/O hybrid ligand: Preparation and use in Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones. J. Org. Chem. 2005, 70 (22), 9009-9012.
19. Ahlbrecht, H.; Sommer, H. Chiral homoenolate equivalents, III: Asymmetric synthesis of 3-substituted 3-phenyl ketones via metalated (S)- methoxymethylpyrrolidine (SMP)-allylamines. Chem. Ber. 1990, 123 (4), 829-836.
20. Brienne, M. J.; Ouannes, C.; Jacques, J. 3-Asymmetric induction, I: Preparation of various ketones with an asymmetric center in the b- and c-position and of known configuration. Bull. Soc. Chim Fr. 1967, 32 (2), 613-623.