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• 1258204-07-7 5-(4-chlorophenyl)hex-5-enoic acid 
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Relevant academic research and scientific papers

Catalytic asymmetric iodocyclization of N-tosyl alkenamides using aminoiminophenoxy copper carboxylate: A concise synthesis of chiral 8-oxa-6-azabicyclo[3.2.1]octanes

A newly developed aminoiminophenoxy copper carboxylate (L7-Cu-OAc)-catalyzed asymmetric iodocyclization of N-Tosyl alkenamides gave O-cyclized products in good yields with high enantioselectivity. From the O-cyclized products, a skeletal transformation was succeeded in the synthesis of biologically important chiral 8-oxa-6-azabicyclo[3.2.1]octanes. DFT calculations suggested that the acetoxy anion of the [L7-Cu-OAc] acts as a base to generate the anion of N-Tosyl alkenamide substrates. The exchanged acetic acid reconstructs a new hydrogen-bonding network between the catalyst and the substrates to accomplish the highly efficient asymmetric O-iodocyclization of N-Tosyl alkenamides. An aminoiminophenoxy copper carboxylate-catalyzed asymmetric iodocyclization of N-Tosyl alkenamides gave O-cyclized products in good yields with high enantioselectivity. Chiral 8-oxa-6-azabicyclo[3.2.1]octanes were synthesized by a sequential reduction/cyclization process from the iodocyclization product. DFT calculations suggested that the N-tosyl alkenamides are activated by hydrogen bonding with a carboxylate anion on the copper center to allow iodo-O-cyclization.

Recyclable Poly-Zn3(OAc)4-3,3′-Bis(aminoimino)binaphthoxide Catalyst for Asymmetric Iodolactonization

On the basis of the structure of the unimolecular Zn3(OAc)4-3,3′-bis(aminoimino)binaphthoxide complex, a poly-Zn3(OAc)4-3,3′-bis(aminoimino)binaphthoxide (poly-Zn) complex was prepared from 3,3′-diformylbinaphth

An asymmetric iodolactonization reaction catalyzed by a zinc bis-proline-phenol complex

The intramolecular zinc bis-proline-phenol complex 2a was found to promote enantioselective iodolactonization reactions of both electron-rich and electron-poor 5-aryl-5-hexenoic acids affording δ-iodolactones in good chemical yields with up to 82% enantio

A trinuclear Zn3(OAc)4-3,3′-bis(aminoimino) binaphthoxide complex for highly efficient catalytic asymmetric iodolactonization

A 3,3′-bis(aminoimino)BINOL ligand was newly designed and synthesized for the formation of a trinuclear Zn complex upon reaction with Zn(OAc) 2. Using the harmony of the tri-zinc atoms, 1 mol% Zn 3(OAc)4-3,3′-bis(aminoimin

The role of ni-carboxylate during catalytic asymmetric iodolactonization using pybidine-ni(OAc)

The combination of a PyBidine-Ni(OAc)2 complex with a catalytic amount of iodine efficiently catalyzed asymmetric iodolactonization to generate chiral iodolactones with up to 89% enantiomeric excess. The formation of an intermediate Ni-carboxylate species from the alkenyl carboxylic acid is a key role in promoting the iodolactonization. Georg Thieme Verlag Stuttgart, New York.

Achiral counterion control of enantioselectivity in a Bronsted acid-catalyzed lactonization

Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Bronsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand-proton complex present at low catalyst loadings) to optimize the enantioselection is documented for the first time in this transformation. In this way, unsaturated carboxylic acids are converted to γ-lactones in high yields (up to 98% ee) using commercially available NIS.