Literature DB >> 23106813

Photoinduced intramolecular cyclopentanation vs photoprotolytic oxametathesis in polycyclic alkenes outfitted with conformationally constrained aroylmethyl chromophores.

Roman A Valiulin1, Teresa M Arisco, Andrei G Kutateladze.   

Abstract

Intramolecular photoinduced cyclizations are investigated in photoprecursors assembled in a modular fashion via a Diels-Alder reaction of acetylenic dienophiles with subsequent Michael additions of aromatic ketones to install a chromophore capable of initiating Paternò-Büchi cycloadditions or radical cyclization cascades. The protolytic oxametathesis in these systems allows for rapid access to novel polycyclic scaffolds decorated by formyl groups and carboxylates suitable for subsequent modifications. In conformationally constrained photoprecursors, a radical rearrangement takes place resulting in intramolecular 1,3-diradical cyclopentanation of the double bond.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 23106813      PMCID： PMC3587035          DOI： 10.1021/jo301909j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  Conformational analysis of singlet-triplet state mixing in Paternò-Büchi diradicals.

Authors:  A G Kutateladze
Journal:  J Am Chem Soc       Date:  2001-09-26       Impact factor: 15.419

2.  An efficient carbonyl-alkene metathesis of bicyclic oxetanes: photoinduced electron transfer reduction of the Paternò-Büchi adducts from 2,3-dihydrofuran and aromatic aldehydes.

Authors:  Raúl Pérez-Ruiz; Miguel A Miranda; Ronald Alle; Klaus Meerholz; Axel G Griesbeck
Journal:  Photochem Photobiol Sci       Date:  2005-12-02       Impact factor: 3.982

3.  Cyclizations of alkynes: revisiting Baldwin's rules for ring closure.

Authors:  Kerry Gilmore; Igor V Alabugin
Journal:  Chem Rev       Date:  2011-08-23       Impact factor: 60.622

4.  Double-tandem [4π+2π]·[2π+2π]·[4π+2π]·[2π+2π] synthetic sequence with photoprotolytic oxametathesis and photoepoxidation in the chromone series.

Authors:  Roman A Valiulin; Teresa M Arisco; Andrei G Kutateladze
Journal:  J Org Chem       Date:  2011-01-26       Impact factor: 4.354

5.  First Example of Intramolecular [2pi+2pi] Alkene-Arene Photocyclization in the Chromone Series and its Synthetic Utility.

Authors:  Roman A Valiulin; Andrei G Kutateladze
Journal:  Tetrahedron Lett       Date:  2010-07-21       Impact factor: 2.415

6.  Strained to the limit: when a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes.

Authors:  Roman A Valiulin; Teresa M Arisco; Andrei G Kutateladze
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

7.  Harvesting the strain installed by a Paternò-Büchi step in a synthetically useful way: high-yielding photoprotolytic oxametathesis in polycyclic systems.

Authors:  Roman A Valiulin; Andrei G Kutateladze
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005
  7 in total
  8 in total

1.  Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction.

Authors:  Jacob R Ludwig; Susan Phan; Christopher C McAtee; Paul M Zimmerman; James J Devery; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-07-28       Impact factor: 15.419

2.  Lewis Acid Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Jacob R Ludwig; Corinna S Schindler
Journal:  Synlett       Date:  2017       Impact factor: 2.454

3.  Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Christopher C McAtee; Paul S Riehl; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-02-21       Impact factor: 15.419

4.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

Authors:  Emilia J Groso; Alexander N Golonka; Ryan A Harding; Brandon W Alexander; Taylor M Sodano; Corinna S Schindler
Journal:  ACS Catal       Date:  2018-01-18       Impact factor: 13.084

5.  Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) Homo-Dimers as Lewis Acidic Superelectrophiles.

Authors:  Haley Albright; Paul S Riehl; Christopher C McAtee; Jolene P Reid; Jacob R Ludwig; Lindsey A Karp; Paul M Zimmerman; Matthew S Sigman; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2019-01-16       Impact factor: 15.419

6.  Brønsted-Acid-Catalyzed Intramolecular Carbonyl-Olefin Reactions: Interrupted Metathesis vs Carbonyl-Ene Reaction.

Authors:  Tanmay Malakar; Paul M Zimmerman
Journal:  J Org Chem       Date:  2021-01-21       Impact factor: 4.354

Review 7.  Carbonyl-Olefin Metathesis.

Authors:  Haley Albright; Ashlee J Davis; Jessica L Gomez-Lopez; Hannah L Vonesh; Phong K Quach; Tristan H Lambert; Corinna S Schindler
Journal:  Chem Rev       Date:  2021-06-16       Impact factor: 72.087

8.  Catalytic, transannular carbonyl-olefin metathesis reactions.

Authors:  Paul S Riehl; Daniel J Nasrallah; Corinna S Schindler
Journal:  Chem Sci       Date:  2019-09-25       Impact factor: 9.825
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.