[go: up one dir, main page]

Kocak et al., 2014 - Google Patents

Norbornanoid chiral ketones by desymmetrization of dibromoalkenes

Kocak et al., 2014

Document ID
17461738146881009175
Author
Kocak R
Borsato G
De Lucchi O
Daştan A
Publication year
Publication venue
Helvetica Chimica Acta

External Links

Snippet

New optically active polycyclic ketones 6a–6d, amenable to a large variety of synthetic applications, have been prepared from readily available 2, 3‐dibromonorbornene and analogs (Scheme 2) via desymmetrization with (−)‐ephedrine, followed by hydrolysis under …
Continue reading at onlinelibrary.wiley.com (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2101/16—The ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2101/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/06—Systems containing only non-condensed rings with a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2102/00—Systems containing two condensed rings
    • C07C2102/02—The rings having only two atoms in common
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2103/00—Systems containing at least three condensed rings
    • C07C2103/02—Ortho- or ortho- and peri-condensed systems
    • C07C2103/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group

Similar Documents

Publication Publication Date Title
Enders et al. Organocatalytic one-pot asymmetric synthesis of functionalized tricyclic carbon frameworks from a triple-cascade/Diels-Alder sequence
Yin et al. Cu (I)-catalyzed decarboxylative aldol-type and Mannich-type reactions for asymmetric construction of contiguous trisubstituted and quaternary stereocenters
US12168224B2 (en) Optically pure enantiomers of ruthenium complexes and uses thereof
US12312361B2 (en) Methods for practical synthesis of deuterated amino acids
Basso et al. Preparation of optically pure fused polycyclic scaffolds by Ugi reaction followed by olefin and enyne metathesis
Kocak et al. Norbornanoid chiral ketones by desymmetrization of dibromoalkenes
Archelas et al. Microbial transformations. 8. First example of a highly enantioselective microbiological hydroxylation process
Essers et al. Enantioselective Diels–Alder reactions of α-fluorinated α, β-unsaturated carbonyl compounds: Part 5. Chemical consequences of fluorine substitution
Piers et al. Methylenecyclohexane annulation. Total synthesis of (±)-axamide-1,(±)-axisonitrile-1, and the corresponding C-10 epimers
Kelch et al. The preparation of several 1, 2, 3, 4, 5-functionalized cyclopentane derivatives
Reddy et al. Enantioselective synthesis of [1, 2]-oxazinone scaffolds and [1, 2]-oxazine core structures of FR900482
Shea et al. Applications of bridgehead alkenes to organic synthesis. Regio-and stereochemical control in the Diels-Alder route to polyfunctional cyclohexenes and cyclohexanes
JP2013245215A (en) Method for producing optically active bicyclic compound based on asymmetric cyclization reaction
Owsianik et al. Three-step synthesis of chiral and sterically hindered amino alcohols based on cyclic enol phosphates
Antolini et al. Synthesis, enzymatic resolution and absolute configuration of ethyl trans-3-(trifluoromethyl) pyroglutamate
Tanaka et al. Optical resolution of 2-azabicyclo [2.2. 1] hept-5-en-3-one by inclusion complexation with brucine
Pfeffer et al. Strategies and methods for the attachment of amino acids and peptides to chiral [n] polynorbornane templates
Corey et al. A simple enantioselective synthesis of (1S, 4R)-bicyclo [2.2. 1] hept-2-ene-2-methanol
Müller et al. A Stereospecific2‐Aza‐divinylcyclopropane'Rearrangement
CN110088094A (en) The method for preparing the pure C9- acetal of alloisomerism
Calmès et al. Asymmetric Diels–Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acid preparation
Wang Highly Stereoselective Cyclopropanation of Alkenes with Unsymmetrical Diazomalonates via Co (II)-Based Metalloradical Catalysis
Titanyuk et al. Synthesis of non-natural cyclic amino acids from available unsaturated tertiary amines
Padgett Rapid Assembly of Complex Cyclohexanes via Asymmetric, Intermolecular Arene Cyclopropanation
Ito Synthetic Utility of Fused-Cyclobutenes: Synthesis of Medium-Sized Cycloalkenes