Journal ArticleDOI
Amino Zinc Enolate Carbocyclization Reactions. New Access to Polysubstituted Piperidine Derivatives.
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TLDR
Various N-pent-4-enylglycine methyl esters have been submitted to carbocyclization of their zinc enolates onto the unactivated double bond, finding a way to di-, tri-, tetra-, or pentasubstituted piperidines.Abstract:
Various N-pent-4-enylglycine methyl esters have been submitted to carbocyclization of their zinc enolates onto the unactivated double bond. The cyclization to substituted pipecolic esters is highly stereoselective. In most cases, substitution of the pent-4-enyl moiety on various sites leads to a single isomer, hence a way to di-, tri-, tetra-, or pentasubstituted piperidines.read more
Citations
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Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids
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Metal mediated carbometallation of alkynes and alkenes containing adjacent heteroatoms
Alex G. Fallis,Pat Forgione +1 more
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Part I: Nitroalkenes in the synthesis of heterocyclic compounds
TL;DR: The applications of nitroalkenes in the synthesis of three to five-membered O, N and S-heterocycles, including natural products are investigated in this paper.
Journal ArticleDOI
Rhenium-Catalyzed Insertion of Terminal Acetylenes into a C−H Bond of Active Methylene Compounds
TL;DR: A rhenium complex catalyzed the intermolecular reactions of 1,3-dicarbonyl compounds with terminal acetylenes and gave the corresponding alkenyl derivatives in excellent yields.
Journal ArticleDOI
First asymmetric total synthesis of (-)-antofine by using an enantioselective catalytic phase transfer alkylation.
TL;DR: The first asymmetric total synthesis of a potential antitumor phenanthroindolizidine alkaloid, (-)-antofine, is described, affording an unnatural alpha-amino acid derivative and a ring closing metathesis for pyrrolidine ring construction.
References
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Journal ArticleDOI
Preparation and reactions of polyfunctional organozinc reagents in organic synthesis
Paul Knochel,Robert D. Singer +1 more
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Synthesis and Reactivity of sp3-Geminated Organodimetallics
Ilan Marek,Jean F. Normant +1 more
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Cyclization of acetylenic alkyllithiums
William F. Bailey,Timo V. Ovaska +1 more
TL;DR: In this paper, the scope and limitations of cyclization reactions involving acetylenic alkyllithiums, which were prepared at -78 o C by lithium-iodine exchange between the corresponding iodide and tert-butyellithium in a solution of n-pentane-diethyl ether (3:2 by volume), have been investigated.
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Preparation and regiospecific cyclization of alkenyllithiums
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New strategy for the synthesis of 3-substituted prolines
TL;DR: In this article, a ring formation involving a 5-exo trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines.