Borane-mediated asymmetric reduction of acetophenone by enantiopure aminonaphthols and aminoalcohols as catalytic source

Chirality

Volumn 22, Issue 7, 2010, Pages 655-661

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

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Aminoalcohols; Aminonaphthols; Asymmetric catalysis; Borane; Ketones; Secondary alchohols

Indexed keywords

ACETOPHENONE; AMINOALCOHOL; AMINONAPHTHOL; BORANE DERIVATIVE; KETONE; LIGAND; NAPHTHOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC REDUCTION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY;

EID: 77952783716     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20812     Document Type: Article

References (14)

1. Corey EJ, Helal CJ. Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: a new paradigm for enantioselective catalysis and a powerful new synthetic method. Angew Chem Int Ed 1998;37:1986-2012.
2. Cho BT. Recent advances in the synthetic applications of the oxazaborolidine-mediated asymmetric reduction. Tetrahedron 2006;62:7621-7643. (Pubitemid 43994021)
3. Singh, VK. Practical and useful methods for the enantioselective reduction of unsymmetrical ketones. Synthesis 1992:607-617.
4. Wallbaum S, Martens J. Asymmetric synthesis with chiral oxazaborolidines. Tetrahedron Asymmetry 1992;3:1475-1504.
5. Hirao A, Itsuno S, Nakahama S, Yamazaki N. Asymmetric reduction of aromatic ketones with chiral alkoxyamine-borane complexes. J Chem Soc Chem Commun 1981:315-317.
6. Corey EJ, Link JO. The first enantioselective syntheses of pure R- and S-isoproterenol. Tetrahedron Lett 1990;31:601-604.
7. Lee D-S. Enantioselective reduction of ketones with borane catalyzed by tridentate amino alcohols derived from salicylaldehyde. Chirality 2007;19:148-151.
8. Narasimhan S, Swarnalakshmi S, Balakumar R, Velmathi S. Novel chiral switching ligands for enantioselective asymmetric reductions of prochiral ketones. Molecules 2001;6:988-995. (Pubitemid 38994456)
9. 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. (Pubitemid 32861787)
10. Cimarelli C, Palmieri G, Volpini E. A practical stereoselective synthesis of secondary and tertiary aminonaphtols: chiral ligands for enentioselective catalysis in the addition of dietilzinc to benzaldehyde. Tetrahedron Asymmetry 2002;13:2417-2426. (Pubitemid 35356475)
11. Cappannini L, Cimarelli C, Giuli S, Palmieri G, Petrini M. Stereoselective synthesis of vicinal aminodiols, diamines and diaminols by the use of enantiopure aldehydes in the three-component aromatic Mannich- type reaction. Tetrahedron: Asymmetry 2007;18:1022-1029.
12. Cimarelli C, Giuli S, Palmieri G. Stereoselective synthesis of enantiopure γ-aminoalcohols by reduction of chiral β-enaminoketones. Tetrahedron: Asymmetry 2006;17:1308-1317.
13. Bartoli G, Cimarelli C, Marcantoni E, Palmieri G, Petrini M. Chemoand diastereoselective reduction of β-enamino esters: a convenient synthesis of both cis- and trans-γ-amino alcohols and β-amino esters. J Org Chem 1994;59:5328-5335. (Pubitemid 24310991)
14. Banphavichit V, Mansawat W, Bhanthumnavin W, Vilaivan T. A highly enantioselective Strecker reaction catalyzed by titanium-N-salicyl-β-amino alcohol complexes. Tetrahedron 2004;60:10559-10568.