TANDEM CARBENE INSERTION SEMIPINACOL REARRANGEMENT OF 1-ALKYNYLCYCLOBUTENOLS - A FACILE SYNTHESIS OF 2-ALKENYL-4-CYCLOPENTENE-1,3-DIONES

Date

1994-02-25

Author

Zora, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

212
views

0
downloads

Reaction of chromium carbene complexes and 1-alkynylcyclobutenols leads to 2-alkenyl-4-cyclopentene-1,3-diones. Initial allkyne insertion affords a highly electrophilic carbene complex, which then undergoes an alkyl shift-ring expansion, ultimately producing 2-alkenyl-4-cyclopentene-1,3-diones.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/34773

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo00083a002

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides Kanberoğlu, Esra; Tanyeli, Cihangir (Wiley, 2015-10-26) A family of chiral bifunctional acid-/base-type quinine/squaramide organocatalysts is shown to be highly active promoters of the conjugate addition of 1-nitropropane to various trans-β-nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 °C by using a catalyst loading of only 2 mol % to afford the 1,3-dinitro Michael adducts with excellent enantioselectivity and diastereoselectivity (up to 95 % ee and syn/anti isomers
Fam-zinc catalyzed asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides and Koyuncu, Hasan; Doğan, Özdemir; Department of Chemistry (2007) In the first part of this study, four new chiral ligands (FAM) were synthesized and used in catalytic amounts in asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides. This method leads to the synthesis of chiral pyrrolidines, which are found in the structure of many biologically active natural compounds and drugs. It was found that using 10 mol% of one of these chiral ligands with different dipolarophiles (dimethyl maleate, dimethyl fumarate, methyl acrylate, tert-butyl acrylate, and Nmethylm...
ANNULATION REACTIONS OF 4-METHOXY-2-PYRONE WITH VARIOUS ACTIVE METHYL COMPOUNDS Tanyeli, Cihangir (Informa UK Limited, 1989-01-01) Some phenolic biphenyl compounds have been synthesised via the annulation reactions of 4-methoxy-2- pyrone with various active methyl compounds.
Asymmetric synthesis of norbornene based 1,4-amino alcohol derivatives and applications in asymmetric transformations Sünbül, Murat; Tanyeli, Cihangir; Department of Chemistry (2005) The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene backbone was performed starting with simple and cheap anhydride 30. Quinine-mediated desymmetrization of anhydride 30 with methanol resulted in (2S,3R)-(-)-cis-hemiester 31 (98% e.e.). Chemoselective amination with HMPTA and NH4OH followed by LAH reduction afforded (2S,3R)-(+)-36 and (2S,3R)-(-)-37, respectively. The amidoester (2S,3R)-(-)-32 was transformed into chiral ligand (2S,3R)-(-)-35 with Grignard reaction followed by LAH reduction. T...
Bicyclic strained allenes : incorporation of an allene unit into alpha-pinene and benzonorbornadiene Kılbaş, Benan; Balcı, Metin; Department of Chemistry (2009) The synthesis of cyclic allenes with eight or less skeletal C-atoms, known as highly strained organic compounds, has for the past decades attracted increasing interest. The first part of study describes an investigation aimed at the incorporation of an allene unit into a natural compound, being α-pinene, by using β-elimination method. The two double-bond isomers 310 and 299b were synthesized as key compounds. Treatment of 310 with t-BuOK resulted in the formation of ketone 308 and diene 313. For the formati...

Citation Formats

M. Zora, “TANDEM CARBENE INSERTION SEMIPINACOL REARRANGEMENT OF 1-ALKYNYLCYCLOBUTENOLS - A FACILE SYNTHESIS OF 2-ALKENYL-4-CYCLOPENTENE-1,3-DIONES,” JOURNAL OF ORGANIC CHEMISTRY, pp. 699–701, 1994, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34773.