Literature DB >> 19215105

Synthesis of 5-hydroxycyclopent-2-enones from allenyl vinyl ketones via an interrupted Nazarov cyclization.

Vanessa M Marx1, D Jean Burnell.   

Abstract

Treatment of an allenyl vinyl ketone with trifluoroacetic acid leads to Nazarov cyclization, and the intermediate carbocation is trapped efficiently by trifluoroacetate. Hydrolysis of the ester with methanol and basic alumina provides, in good to excellent overall yield, a 5-hydroxycyclopent-2-enone in which the alcohol is predominantly trans to a substituent at C-4.

Entities:  

Year:  2009        PMID： 19215105     DOI： 10.1021/ol900029d

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


  8 in total

1.  Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors:  David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-26       Impact factor: 15.336

2.  Efficient Nazarov cyclization/Wagner-Meerwein rearrangement terminated by a Cu(II)-promoted oxidation: synthesis of 4-alkylidene cyclopentenones.

Authors:  David Lebœuf; Eric Theiste; Vincent Gandon; Stephanie L Daifuku; Michael L Neidig; Alison J Frontier
Journal:  Chemistry       Date:  2013-02-21       Impact factor: 5.236

3.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       Impact factor: 15.419

4.  Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

Authors:  John A Malona; Kevin Cariou; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

5.  Studies on the Himbert intramolecular arene/allene Diels-Alder cycloaddition. Mechanistic studies and expansion of scope to all-carbon tethers.

Authors:  Yvonne Schmidt; Jonathan K Lam; Hung V Pham; K N Houk; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2013-05-01       Impact factor: 15.419

6.  Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

Authors:  William F Bow; Ashok K Basak; Anais Jolit; David A Vicic; Marcus A Tius
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

7.  CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands.

Authors:  Shuxu Gao; Yu Liu; Shengming Ma
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

8.  Substrate-controlled selectivity switch in a three-component reaction: sequential synthesis of spiro-oxazolidinedione-cyclopentenones and hydroxy enaminobarbiturates in water.

Authors:  Mohammad Bagher Teimouri; Mahdi Heydari; Kazem Mohammadi
Journal:  RSC Adv       Date:  2020-04-03       Impact factor: 4.036
  8 in total

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