Erratum to "Hydroxyamide-catalyzed enantioselective addition of diethylzinc to benzaldehyde in the absence of titanium". [Tetrahedron: Asymmetry 19 (2008) 646] (DOI:10.1016/j.tetasy.2008.02.025);Hydroxyamide-catalyzed enantioselective addition of diethylzinc to benzaldehyde in the absence of titanium

Tetrahedron Asymmetry

Volumn 19, Issue 6, 2008, Pages 646-650

  de las Casas Engel, Tomás ^a   Lora Maroto, Beatriz ^a   García Martínez, Antonio ^a   de la Moya Cerero, Santiago ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZALDEHYDE; CAMPHOR; DIETHYLZINC; HYDROXYAMIDE; ISOBORNEOL; TITANIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 41449083639     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.07.002     Document Type: Erratum

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37. 2 (5.2 mmol) were refluxed in anhydrous THF for 15 min. The reaction mixture was then cooled down to 0 °C and, triethylamine (10.5 mmol) and piperidine (5.0 mmol), or N,N′-dimethylethane-1,2-diamine (2.5 mmol), or piperazine (2.5 mmol), slowly added. The reaction mixture was then stirred for 1 h at rt. Standard work-up (extraction and acid- and base-washing) yielded pure amide in ca. 85% yield for both the cases. Spectroscopic data agree with the corresponding structure. Piperazine-based ketoamide has been previously-reported by Aoyama (see Ref. 12) as a synthetic intermediate.
38. 4 reduction in refluxing THF (for example, see Ref. 11). Yield: 80% for the obtention of 6, 63% for the obtention of 7, and 91% for the obtention of 8.
39. Under argon, diethylzinc (1.0 M in hexane, 2 mL, 2.0 mmol) was added to the corresponding ligand (0.050 mmol) in anhydrous hexane (1 mL) and the mixture stirred for 1 h at rt. Freshly distilled benzaldehyde (1.0 mmol) was then slowly added and the resulting mixture stirred for 5 h at rt. Final treatment with 1 M HCl at 0 °C and standard work-up (for example, see Ref. 12) yielded the resulting enantioenriched mixture of 1-phenylpropan-1-ol. The ee was determined by GC (cyclodex-B). The dominant configuration was determined by both the sign of the mixture's specific rotation and the elution time on chiral GC.
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42. endo versus exo Indicates the coordination face of the reacting species to the catalyst's Zn-O bond. syn versus anti Indicates the relative disposition of both the zinc ethyl groups. Re versus Si indicates the carbonyl face on which the ethyl transfer occurs.
43. 2 chelate, can be possible.