Literature DB >> 22098535

Iron-catalyzed rearrangements and cycloaddition reactions of 2H-chromenes.

Yi Luan1, Huan Sun, Scott E Schaus.   

Abstract

Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.

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Year:  2011        PMID： 22098535      PMCID： PMC4655818          DOI： 10.1021/ol202772k

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


  16 in total

1.  Unexpected iron(III) chloride-catalysed dimerisation of 1,1,3-trisubstituted-prop-2-yn-1-ols as an expedient route to highly conjugated indenes.

Authors:  Weidong Rao; Philip Wai Hong Chan
Journal:  Org Biomol Chem       Date:  2010-07-20       Impact factor: 3.876

2.  Josiphos-catalyzed asymmetric homodimerization of ketoketenes.

Authors:  Ahmad A Ibrahim; Pei-Hsun Wei; Gero D Harzmann; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

Review 3.  Iron-catalyzed reactions in organic synthesis.

Authors:  Carsten Bolm; Julien Legros; Jacques Le Paih; Lorenzo Zani
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

4.  Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide.

Authors:  Lee M Bishop; Michael Winkler; Kendall N Houk; Robert G Bergman; Dirk Trauner
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

5.  Structures of two natural hypotensive Diels-Alder type adducts, mulberrofurans F and G, from the cultivated mulberry tree (Morus lhou KOIDZ.).

Authors:  T Fukai; Y Hano; K Hirakura; T Nomura; J Uzawa; K Fukushima
Journal:  Chem Pharm Bull (Tokyo)       Date:  1985-08       Impact factor: 1.645

6.  A convergent total synthesis of (±)-γ-rubromycin.

Authors:  Kun-Liang Wu; Eduardo V Mercado; Thomas R R Pettus
Journal:  J Am Chem Soc       Date:  2011-03-31       Impact factor: 15.419

7.  ortho-Quinone methides from para-quinones: total synthesis of rubioncolin B.

Authors:  Jean-Philip Lumb; Kevin C Choong; Dirk Trauner
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

8.  Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

Authors:  Maurice A Marsini; Yaodong Huang; Christopher C Lindsey; Kun-Liang Wu; Thomas R R Pettus
Journal:  Org Lett       Date:  2008-03-13       Impact factor: 6.005

9.  NMR kinetic investigations of the photochemical and thermal reactions of a photochromic chromene.

Authors:  Stéphanie Delbaere; Jean-Claude Micheau; Gaston Vermeersch
Journal:  J Org Chem       Date:  2003-11-14       Impact factor: 4.354

10.  C-H bond functionalization via hydride transfer: synthesis of dihydrobenzopyrans from ortho-vinylaryl akyl ethers.

Authors:  Kevin M McQuaid; Jonathan Z Long; Dalibor Sames
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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  3 in total

1.  The development of a novel HAuCl4@MOF catalyst and its catalytic application in the formation of dihydrochalcones.

Authors:  Yi Luan; Yue Qi; Jie Yu; Hongyi Gao; Scott E Schaus
Journal:  RSC Adv       Date:  2014-07-28       Impact factor: 3.361

2.  Multicomponent Condensation Reactions via ortho-Quinone Methides.

Authors:  Emily E Allen; Calvin Zhu; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

3.  4-Amino-8-cyclo-pent-yloxy-7-meth-oxy-2H-chromen-2-one monohydrate.

Authors:  Man-Hua Ding; Xiao-Ping Jiang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-18
  3 in total

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