Design and synthesis of chiral hybrid spiro (isoxazole-isoxazoline) ligands

Tetrahedron Asymmetry

Volumn 18, Issue 8, 2007, Pages 919-923

  Koranne, Priti S ^a   Tsujihara, Tetsuya ^a   Arai, Midori A ^a   Bajracharya, Gan B ^a   Suzuki, Takeyuki ^a   Onitsuka, Kiyotaka ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKENYL GROUP; DECANE; ISOXAZOLE DERIVATIVE; ISOXAZOLINE DERIVATIVE; LEAD; LIGAND; SPIRO COMPOUND;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 34249314067     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.04.010     Document Type: Article

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35. * diastereomer.
36. 2. The resulting diastereomers 2 and 2′ were easily separated by silica gel column chromatography.
37. 1H NMR analyses and TLC behaviour was used to identify the required diastereomer.
38. +]: 303.2073; found, 303.2095. Mp 116 °C (recrystallization from hexane/ether).
39. Crystallographic data (excluding structure factors) for the structure 2c in this paper have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number CCDC 640619. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 lEZ, UK [fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]. The absolute configurations of ligands 2 and 2′ were not determined.
40. Conditions for HPLC separation [Daicel Chiralpak AD column (2 cm Φ × 25 cm)]: Compound 2a; hexane/EtOH (7:3), flow rate = 2.5 mL/min, 34 min, 48 min. Compound 2b: hexane/i-PrOH (9:1), flow rate = 2.5 mL/min, 21 min, 33 min. Compound 2c: hexane/i-PrOH (9:1), flow rate = 2.5 mL/min, 14 min, 22 min. Compound 2d: hexane/i-PrOH (9:1), flow rate = 2.5 mL/min, 10 min, 16 min. Compound 2e: hexane/i-PrOH (9:1), flow rate = 2.5 mL/min, 8 min, 14 min.
41. 1H NMR.
42. A plausible mechanism of the tandem cyclization is discussed in Ref. 3.
43. The ee of product 9, checked after 2, 8 and 12 h, was found to be constant (95%).
44. 2 proved to be the best Pd sources.
45. 2/MeOH (1:1), rt, 192 h.