Journal ArticleDOI
Diastereoselektive Synthese von β‐Methyl‐homoallylalkoholen durch lk‐Addition von (2‐Butenyl)triphenoxytitan an Aldehyde
L. Widler,Dieter Seebaeh +1 more
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TLDR
In this paper, the 2-butenylmagnesium halogenide and chlorotriphenoxytitanium in tetrahydrofuran solution was added to aldehydes with like (Re,Re/Si,SiRe*,Re*) relative topicity in diastereoselectivities.Abstract:
Diastereoselective Synthesis of β-Methyl-homoallylic Alcohols by lk-Addition of (2-Butenyl)triphenoxytitanium to Aldehydes
(2-Butenyl)triphenoxytitanium, prepared in situ from (2-butenyl)magnesium halogenide and chlorotriphenoxytitanium in tetrahydrofuran solution, adds to aldehydes with like (Re,Re/Si,SiRe*,Re*) relative topicity in diastereoselectivities of 80–99%.read more
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The Unambiguous Specification of the Steric Course of Asymmetric Syntheses
Dieter Seebach,Vladimir Prelog +1 more
TL;DR: In this article, the relative topicity of approach of reactants is defined as like {Ik} and unlike (ul) if the corresponding descriptor pairs are Re*,Re*. or R*,Re*, and Re*,Si* or R*)Si*, respectively.
Journal ArticleDOI
Diastereogenic Addition of Crotylmetal Compounds to Aldehydes
TL;DR: In this article, the authors proposed a stereoselective CC bond forming reaction to obtain a diastereomeric adduct from E- or Z-crotyl compounds.
Journal ArticleDOI
Enantioselective syntheses with titanium carbohydrate complexes. Part 7. Enantioselective allyltitanation of aldehydes with cyclopentadienyldialkoxyallyltitanium complexes
Andreas Hafner,Rudolf O. Duthaler,Roger Marti,Grety Rihs,Petra Rothe-Streit,Franz Schwarzenbach +5 more
TL;DR: In this article, the preparation, analysis, and reactions of novel, highly stereoselective cyclopentadienyldialkoxyallyltitanium reagents, available in both enantiomeric forms, are described.
Journal ArticleDOI
Organometallic Compounds of Titanium and Zirconium as Selective Nucleophilic Reagents in Organic Synthesis
Beat Weidmann,Dieter Seebach +1 more
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Spezifikation des sterischen Verlaufs von asymmetrischen Synthesen
Dieter Seebach,Vladimir Prelog +1 more
TL;DR: In this paper, Cahn-Ingold-Prelog-System basierendes Verfahren zur eindeutigen spezifikation des sterischen Verlaufs sowie der Produktkonfiguration von asymmetrischen Synthesen, vor allem von diastereoselektiven Reaktionen vor: die reflexionsinvariante relative Topizitat der gegenseitigen Annaherung von Reaktanden wird als lk (like)
References
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Synthesis of Open-Chain 2,3-Disubstituted 4-nitroketones by Diastereoselective Michael-addition of (E)-Enamines to (E)-Nitroolefins. A topological rule for C, C-bond forming processes between prochiral centres. Preliminary communication
Dieter Seebach,Jerzy Goliński +1 more
TL;DR: In this paper, the Michael-additions of aliphatic, alicyclic, and arylsubstituted nitroolefins and enamines lead to γ-nitroketones 3 in good chemical and excellent (> 90%) diastereomeric yields.
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Chiral enolate design
TL;DR: In this article, the basic design features associated with the construction of chiral propionate enolates are presented and general transition state models for predictable chirality transfer are presented during the course of the discussion.
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Erythro-selective addition of crotyltrialkyltins to aldehydes regardless of the geometry of the crotyl unit. Stereoselection independent of the stereochemistry of precursors
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Acyclic Stereocontrol Through the Aldol Condensation
TL;DR: One of the oldest organic reactions, the aldol condensation, is emerging as a powerful tool for use in achieving stereocontrol in the synthesis of acyclic and other conformationally flexible molecules.
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Chromium(II) mediated threo selective synthesis of homoallyl alcohols
TL;DR: In this article, remarkable threo selectivity was observed in the reaction of aldehydes with trans-and cis-1-bromo-2-butene with the aid of chromium-II salts.