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Literature DB >> 16819843

Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

Abstract

A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16819843 PMCID： PMC2596606 DOI： 10.1021/ja0609046

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

3 in total

1. Enantiopure N-acyldihydropyridones as synthetic intermediates: asymmetric synthesis of benzomorphans.

Authors: D L Comins; Y M Zhang; S P Joseph
Journal: Org Lett Date: 1999-08-26 Impact factor: 6.005

2. Synthesis of the quinolizidine alkaloids (-)-lasubine II and (+/-)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones.

Authors: Thomas G Back; Michael D Hamilton; Vania J J Lim; Masood Parvez
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

3. Stereoselective convergent synthesis of a trans-fused polycyclic ether ring system including a 4-hydroxy-5-methyl-tetrahydropyran ring.

Authors: Keisuke Suzuki; Tadashi Nakata
Journal: Org Lett Date: 2002-08-08 Impact factor: 6.005

3 in total

16 in total

1. Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors: Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal: J Org Chem Date: 2010-10-15 Impact factor: 4.354

2. Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

Authors: Hajime Seki; Gunda I Georg
Journal: European J Org Chem Date: 2014-06-01

3. Three-component synthesis of cyclic enaminones via ketene cyclization.

Authors: Hajime Seki; Gunda I Georg
Journal: Org Lett Date: 2011-04-01 Impact factor: 6.005

4. Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors: Micah J Niphakis; Gunda I Georg
Journal: J Org Chem Date: 2010-09-03 Impact factor: 4.354

5. Synthesis of a 3-Amino-2,3-dihydropyrid-4-one and Related Heterocyclic Analogues as Mechanism-Based Inhibitors of BioA, a Pyridoxal Phosphate-Dependent Enzyme.

Authors: Carter G Eiden; Courtney C Aldrich
Journal: J Org Chem Date: 2017-07-26 Impact factor: 4.354

Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

1. Enantiopure N-acyldihydropyridones as synthetic intermediates: asymmetric synthesis of benzomorphans.

2. Synthesis of the quinolizidine alkaloids (-)-lasubine II and (+/-)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones.

3. Stereoselective convergent synthesis of a trans-fused polycyclic ether ring system including a 4-hydroxy-5-methyl-tetrahydropyran ring.

1. Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

2. Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

3. Three-component synthesis of cyclic enaminones via ketene cyclization.

4. Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

5. Synthesis of a 3-Amino-2,3-dihydropyrid-4-one and Related Heterocyclic Analogues as Mechanism-Based Inhibitors of BioA, a Pyridoxal Phosphate-Dependent Enzyme.

6. Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A.

7. Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP.

8. Microwave-assisted Suzuki-Miyaura couplings on α-iodoenaminones.

9. Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

10. Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.