A free radical approach to the synthesis of the 1,7-dioxaspiro[4,4]nonane ring system from carbohydrate templates

Tetrahedron Asymmetry

Volumn 14, Issue 19, 2003, Pages 2865-2869

  Marco Contelles, José ^a   Domínguez, Laura ^a   Anjum, Shazia ^a,d   Ballesteros, Paloma ^b   Soriano, Elena ^b   Postel, Denis ^c  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^c UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^d PCSIR LABORATORIES COMPLEX   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

1,7 DIOXASPIRO[4.4]NONANE; ALKANE DERIVATIVE; CARBOHYDRATE DERIVATIVE; FREE RADICAL; PHENYL GROUP; TRIPHENYLTIN HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; HYDROXYLATION; PRECURSOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; RING OPENING; SYNTHESIS;

EID: 1842578433     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.06.002     Document Type: Article

References (23)

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19. The authors propose that the highly oxygenated substrates in this study react with n-BuLi, to form intermediate chelate lithium complexes, which inhibit the normal protodestannylation reaction. It is felt that this unexpected result deserves a more detailed study, hence such work is currently being pursued in our laboratory.
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22. (a) All structures were optimized and characterized by vibrational analysis with a UHF/PM3 model. At this level, we also determined the ZPE, thermal correction to enthapy and entropy. (b) We performed single-point calculations over the optimized geometries with the UB3LYP hybrid functional, by using the LANL2DZ basis set for Sn, which includes a 46 core electron relativistic ECP, and the 3-21G basis set for the other atoms.
23. Similar conclusions were obtained from structure D2.