Literature DB >> 19731959

Rhodium-catalyzed ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with arylboronic acids.

Ben P Machin1, Melissa Ballantine, Jérémie Mandel, Nicolas Blanchard, William Tam.   

Abstract

Rhodium-catalyzed ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with arylboronic acids were investigated. The use of [RhCl(COD)](2), (+/-)-BINAP, and NaHCO(3) in MeOH at 60 degrees C was found to be the optimized conditions for the ring-opening reactions to give the 1,2-ring-opened products. Various arylboronic acids were examined, and low to moderate yields were obtained and stereoselectivities (trans/cis) from 50:50 to 100:0 were observed.

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Year:  2009        PMID： 19731959     DOI： 10.1021/jo901248w

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


  4 in total

1.  Regio- and stereochemically controlled formation of hydroxamic acids from indium triflate-mediated nucleophilic ring-opening reactions with acylnitroso-Diels-Alder adducts.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-02-10       Impact factor: 2.415

2.  Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors:  Cheng Ji; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

3.  Indium triflate-assisted nucleophilic aromatic substitution reactions of nitrosobezene-derived cycloadducts with alcohols.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

4.  Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols.

Authors:  Katrina Tait; Alysia Horvath; Nicolas Blanchard; William Tam
Journal:  Beilstein J Org Chem       Date:  2017-12-27       Impact factor: 2.883
  4 in total

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