Stereocontrolled Synthesis of Spiroketals via Ti(Oi-Pr)-Mediated Kinetic Spirocyclization of Glycal Epoxides with Retention of Configuration.
The article discusses the stereocontrolled synthesis of spiroketals. It is observed that alternate nonchelated mechanisms are inconsistent with the observed stereochemical preference. Kinetic spiroketalization is Mediated cyclization of Ti(Oi-Pr)4 and MeOH-induced cyclization (C1-inversion) provide...
| Publicado en: | Journal of the American Chemical Society Vol. 128; no. 6; pp. 1792 - 1794 |
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| Autores principales: | , , |
| Formato: | Artículo |
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American Chemical Society
2/15/2006
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| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=20080004&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 20080004 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 2/15/2006 vid: 128 iid: 6 pid: 997 pub: American Chemical Society artinfo: ui: 20080004 10.1021/ja057908f ppf: 1792 ppct: 2 formats: tig: atl: Stereocontrolled Synthesis of Spiroketals via Ti(Oi-Pr)-Mediated Kinetic Spirocyclization of Glycal Epoxides with Retention of Configuration. aug: au: Moilanen, Sirkka B. Potuzak, Justin S. Tan, Derek S. affil: Tri-Institutional Training Program in Chemical Biology. Pharmacology Program Weill Graduate School of Medical Sciences of Cornell University. Tri-Institutional Research Program and Molecular Pharmacology & Chemistry Program, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York. su: Chemical kinetics Ring formation (Chemistry) Reaction mechanisms (Chemistry) Occlusal adjustment Chemical reactions Substitution reactions sug: subj: Chemical kinetics Ring formation (Chemistry) Reaction mechanisms (Chemistry) Occlusal adjustment Chemical reactions Substitution reactions ab: The article discusses the stereocontrolled synthesis of spiroketals. It is observed that alternate nonchelated mechanisms are inconsistent with the observed stereochemical preference. Kinetic spiroketalization is Mediated cyclization of Ti(Oi-Pr)4 and MeOH-induced cyclization (C1-inversion) provide comprehensive access to systematically stereochemically diversified spiroketals. The exposure of the inversion spiroketal to the reaction conditions did not result in equilibration which shows that Ti(Oi-Pr)4-mediated spirocyclization is, kinetically controlled. Reduced stereoselectivity was observed when substoichiometric amounts of Ti(Oi-Pr)4 was used suggesting that the metal may remain coordinated to the product , although the complex is not responsible for the stereochemical outcome of the kinetically reaction. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2006 holdings: @attributes: islocal: N |
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