Literature DB >> 27558964

Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition.

Michael L Conner1, M Kevin Brown1.   

Abstract

A method for the [2 + 2] cycloaddition of terminal alkenes with allenoates is presented. This process allows for the rapid synthesis of 1,3-substituted cyclobutanes in high yield under simple and robust reaction conditions.

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Year:  2016        PMID： 27558964      PMCID： PMC5534137          DOI： 10.1021/acs.joc.6b01446

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


  32 in total

1.  Enantiomerically pure cyclobutane derivatives and their use in organic synthesis.

Authors:  Edward Lee-Ruff; Gabriela Mladenova
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Electrochemically supported deoxygenation of epoxides into alkenes in aqueous solution.

Authors:  Jing-Mei Huang; Zhi-Quan Lin; Dong-Song Chen
Journal:  Org Lett       Date:  2011-12-07       Impact factor: 6.005

3.  ORGANIC CHEMISTRY. Iron-catalyzed intermolecular [2+2] cycloadditions of unactivated alkenes.

Authors:  Jordan M Hoyt; Valerie A Schmidt; Aaron M Tondreau; Paul J Chirik
Journal:  Science       Date:  2015-08-28       Impact factor: 47.728

4.  Oxetanes as promising modules in drug discovery.

Authors:  Georg Wuitschik; Mark Rogers-Evans; Klaus Müller; Holger Fischer; Björn Wagner; Franz Schuler; Liudmila Polonchuk; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

5.  Discovery of two clinical histamine H(3) receptor antagonists: trans-N-ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidinylmethyl)phenyl]cyclobutanecarboxamide (PF-03654746) and trans-3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]-N-(2-methylpropyl)cyclobutanecarboxamide (PF-03654764).

Authors:  Travis T Wager; Betty A Pettersen; Anne W Schmidt; Douglas K Spracklin; Scot Mente; Todd W Butler; Harry Howard; Daniel J Lettiere; David M Rubitski; Diane F Wong; Frank M Nedza; Frederick R Nelson; Hans Rollema; Jeffrey W Raggon; Jiri Aubrecht; Jody K Freeman; John M Marcek; Julie Cianfrogna; Karen W Cook; Larry C James; Linda A Chatman; Philip A Iredale; Michael J Banker; Michael L Homiski; Jennifer B Munzner; Rama Y Chandrasekaran
Journal:  J Med Chem       Date:  2011-10-07       Impact factor: 7.446

6.  Toward ideality: the synthesis of (+)-kalkitoxin and (+)-hydroxyphthioceranic acid by assembly-line synthesis.

Authors:  Sebastien Balieu; Gayle E Hallett; Matthew Burns; Teerawut Bootwicha; John Studley; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2015-01-27       Impact factor: 15.419

7.  Rhodium-catalyzed rearrangement of alpha-diazo thiol esters to thio-substituted ketenes. Application in the synthesis of cyclobutanones, cyclobutenones, and beta-lactams.

Authors:  M D Lawlor; T W Lee; R L Danheiser
Journal:  J Org Chem       Date:  2000-07-14       Impact factor: 4.354

8.  Replacement of Thr32 and Gln34 in the C-terminal neuropeptide Y fragment 25-36 by cis-cyclobutane and cis-cyclopentane β-amino acids shifts selectivity toward the Y(4) receptor.

Authors:  Lukasz Berlicki; Melanie Kaske; Raquel Gutiérrez-Abad; Günther Bernhardt; Ona Illa; Rosa M Ortuño; Chiara Cabrele; Armin Buschauer; Oliver Reiser
Journal:  J Med Chem       Date:  2013-10-25       Impact factor: 7.446

9.  Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors:  Scott N Mlynarski; Alexander S Karns; James P Morken
Journal:  J Am Chem Soc       Date:  2012-09-24       Impact factor: 15.419

10.  Cyclobutane and cyclobutene synthesis: catalytic enantioselective [2+2] cycloadditions.

Authors:  Yao Xu; Michael L Conner; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-02       Impact factor: 15.336
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  6 in total

1.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

2.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

3.  Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds.

Authors:  Taeho Kang; Tuğçe G Erbay; Kane L Xu; Gary M Gallego; Alexander Burtea; Sajiv K Nair; Ryan L Patman; Ru Zhou; Scott C Sutton; Indrawan J McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2020-10-27       Impact factor: 13.084

4.  Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes.

Authors:  Yanyao Liu; Dongshun Ni; Bernard G Stevenson; Vikrant Tripathy; Sarah E Braley; Krishnan Raghavachari; John R Swierk; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-21       Impact factor: 16.823

5.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005

6.  Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes.

Authors:  Zeguo Fang; Nawaf Al-Maharik; Peer Kirsch; Matthias Bremer; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2020-04-14       Impact factor: 2.883
  6 in total

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