Enantiomerically pure γ-oxidofunctionalised organolithium compounds from chiral oxetanes

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2633-2643

  Bachki, Abderrazak ^a   Falvello, Larry R ^b   Foubelo, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOLITHIUM COMPOUND; OXETANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030849918     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00274-7     Document Type: Article

References (60)

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47. c)/3. The convergent refinement (ave., max. Δ/σ=0.002,0.021) gave R1=0.1236, wR2=0.3337, and quality-of-fit=1.116. Twin models were tested for hypothetical two-fold twin axes along [100], [101], and [001], and for a hypothetical 3-fold twin axis along [010]. None of these models led to improvement of the agreement factors. The absolute configuration was established by the known stereochemistries at chiral carbon atoms C(1), C(4), C(21), and C(24). Detailed structural results have been deposited at the Cambridge Crystallographic Data Centre.
48. (b) Diffractometer control program: CAD4-PC Version 2.0, ©1996, Delft Instruments X-ray Diffraction bv, Delft, The Netherlands.
49. (c) Data were processed on an AlphaStation 200 4/166 (AlphaVMS V6.2), with the program XCAD4B (K. Harms, University of Marburg) and with the commercial package SHELXTL-PLUS Release 5.05/V: ©1996, Siemens Analytical X-ray Instruments, Inc., Madison, Wisconsin. Further calculations were done on a Hewlett-Packard 9000 Model 715/50 (HP-UX V9.05).
50. (d) Shelxl-96 (Version beta 2): FORTRAN-77 program for the refinement of crystal structures from diffraction data: ©1996, George M. Sheldrick.
51. (e) H. D. Flack and D. Schwarzenbach, Acta Cryst. Section A 1988, A44, 499-506.
52. Last paper from our laboratory in this field: Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron: Asymmety 1996, 7, 2997-3008.
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54. Oxetanes 4 and 7 are not enantiomerically pure compounds. They are a ca. 1:1 diastereomeric mixture due to the new stereogenic centre, which has been created at the ketalic carbon during the protection reaction of the alcohol with dihydropyran.
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56. See, for instance: (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
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58. Almena, J.; Foubelo, F.; Yus, M. J. Org. Chem. 1994, 59, 3210-3215.
59. Mixture of diastereoisomers, which could not be separated by flash chromatography or in TLC.
60. + signal.