Literature DB >> 20608636

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

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

Abstract

Strained polycyclic oxetanes generated photochemically from the Diels-Alder adducts of cyclic dienes and enones undergo deep skeletal rearrangements under protolytic ring-opening conditions offering expeditious access to chlorohydrins and other products of unique skeletal topology.

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Year:  2010        PMID： 20608636      PMCID： PMC2912957          DOI： 10.1021/ol101297b

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  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

2.  Searching for intermediates in Prins cyclisations: the 2-oxa-5-adamantyl carbocation.

Authors:  Roger W Alder; Fabrizio Carta; Christopher A Reed; Irina Stoyanova; Christine L Willis
Journal:  Org Biomol Chem       Date:  2010-01-28       Impact factor: 3.876

3.  The first general enantioselective catalytic Diels-Alder reaction with simple alpha,beta-unsaturated ketones.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

4.  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
  4 in total
  5 in total

1.  Programmable enantioselective one-pot synthesis of molecules with eight stereocenters.

Authors:  Marco Potowski; Markus Schürmann; Hans Preut; Andrey P Antonchick; Herbert Waldmann
Journal:  Nat Chem Biol       Date:  2012-03-18       Impact factor: 15.040

2.  Photoassisted access to enantiopure conformationally locked ribofuranosylamines spiro-linked to oxazolidino-diketopiperazines.

Authors:  Nitin S Nandurkar; N N Bhuvan Kumar; Olga A Mukhina; Andrei G Kutateladze
Journal:  ACS Comb Sci       Date:  2012-12-04       Impact factor: 3.784

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

Authors:  Roman A Valiulin; Teresa M Arisco; Andrei G Kutateladze
Journal:  J Org Chem       Date:  2012-11-07       Impact factor: 4.354

4.  Design and synthesis of fused polycycles via Diels-Alder reaction and ring-rearrangement metathesis as key steps.

Authors:  Sambasivarao Kotha; Ongolu Ravikumar
Journal:  Beilstein J Org Chem       Date:  2015-07-27       Impact factor: 2.883

Review 5.  Recent applications of ring-rearrangement metathesis in organic synthesis.

Authors:  Sambasivarao Kotha; Milind Meshram; Priti Khedkar; Shaibal Banerjee; Deepak Deodhar
Journal:  Beilstein J Org Chem       Date:  2015-10-07       Impact factor: 2.883
  5 in total

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