Journal ArticleDOI
Alkyl-, Aryl-, Vinyl-, and Heterosubstituted Organozirconium Compounds. -Selective nucleophiles of low basicity. Preliminary communication
TLDR
In contrast to their titanium analogues, vinylzirconium reagents are stable enough to be employed. as discussed by the authors showed that aldehyde and ketone carbonylophiles of exceedingly low basicity can be solved from aldehydes and aldeheeds using trialkoxyzircimiconium chloride.Abstract:
Solutions of the title compounds are accessible from organolithium reagents and trialkoxyzirconium chloride (equation 2). In contrast to their titanium analogues, vinylzirconium reagents are stable enough to be employed. Generally, organozirconium reagents are highly selective aldehyde and ketone carbonylophiles of exceedingly low basicity (Tables 1, 2, 3 and typical procedure).read more
Citations
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Journal ArticleDOI
Organocerium reagents. Nucleophilic addition to easily enolizable ketones
TL;DR: Organocerium reagents, prepared from organolithiums and anhydrous cerium (III) chloride, react cleanly with easily enolizable ketones to afford the addition products in good to excellent yields as discussed by the authors.
Journal ArticleDOI
Organometallic Compounds of Titanium and Zirconium as Selective Nucleophilic Reagents in Organic Synthesis
Beat Weidmann,Dieter Seebach +1 more
Journal ArticleDOI
Synthesis of D-Erythro- and D-Threo-Sphingosine Derivatives From L-Serine
TL;DR: In this paper, the protected serine aldehyde 10 was converted to the crystalline N-Boc-protected sphingosines 6-9 by a three-step reaction sequence.
Journal ArticleDOI
Chemoselective addition of organotitanium reagents to carbonyl compounds
Manfred T. Reetz,Jürgen Westermann,Rainer Steinbach,B. Wenderoth,Roland Peter,Ralph Ostarek,Sabina Maus +6 more
TL;DR: The standard titanating agent is chlorotrisopropoxytitanium (1) as mentioned in this paper, which is aldehyde-selective in the presence of aldehydes.
Journal ArticleDOI
Organometallverbindungen von Titan und Zirconium als selektive nucleophile Reagentien für die Organische Synthese
Beat Weidmann,Dieter Seebach +1 more
TL;DR: In this paper, the authors unterscheiden sich die Geschwindigkeiten der Reaktionen of CH3Ti(OiPr)3 with Benzaldehyd and with Acetophenon bei Raumtemperatur um mehr als funf Zehnerpotenzen.
References
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Journal ArticleDOI
Methoden der Reaktivitätsumpolung
TL;DR: The Umpolung der Reaktivitat wurde als nutzliches heuristisches Prinzip, als Einteilungsschema und als Leitfaden zum Auffinden strategischer Bindungen erkannt (Synthon-, Transform-and Retrosynthesebetrachtungen nach Corey) as mentioned in this paper.
Journal ArticleDOI
Thermal decomposition of vinylic copper(I) and silver(I) organometallic compounds
TL;DR: In this paper, it was shown that free propenyl radicais are not intermediates in these thermal coupling re-ttctions, when interpreted in light of the known rate of inversion of configuration of vinylradicirls.
Journal ArticleDOI
Methyl‐triisopropoxy‐titanium, a highly selective nucleophilic methylating reagent. Preliminary Communication
Beat Weidmann,Dieter Seebach +1 more
TL;DR: Replacement of lithium or magnesium by titanium can furnish nucleophilic organometallic reagents of high selectivity as exemplified by the title compound 1 (see Tables 1 and 3) as discussed by the authors.
Journal ArticleDOI
Selectivities in the Reactions of Alkyl‐, Aryl‐ and Heterosubstituted Organotitanium Compounds Preliminary Communication
TL;DR: In this article, it was shown that some heterosubstituted organotitanium compounds are more stable thermally than their lithium counterparts, and that with the chiral (S)-2-methyl-l-butoxy group an enantioselective addition can be achieved.
Journal ArticleDOI
3‐Hydroxy‐4‐nitro‐cyclohexanone aus Ketonen und 4‐Nitrobuttersäurechlorid. Eine ringerweiternde Fünfringanellierung
TL;DR: In this article, a ring enlargement of a cyclic ketone by one C-atom was carried out with simultaneous annulation of cyclopentanone ring with nitrobutanoic acid and subsequent rearrangement.
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Organometallic Compounds of Titanium and Zirconium as Selective Nucleophilic Reagents in Organic Synthesis
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Organometallverbindungen von Titan und Zirconium als selektive nucleophile Reagentien für die Organische Synthese
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Methyl‐triisopropoxy‐titanium, a highly selective nucleophilic methylating reagent. Preliminary Communication
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