Literature DB >> 23952128

Synthesis of trans-2-(trifluoromethyl)cyclopropanes via Suzuki reactions with an N-methyliminodiacetic acid boronate.

Matthew A J Duncton1, Rajinder Singh.   

Abstract

trans-2-(Trifluoromethyl)cyclopropylboronic acid N-methyliminodiacetic acid (MIDA) ester 5 was synthesized as a pure diastereomer from vinylboronic acid MIDA ester and (trifluoromethyl)diazomethane in a single step. An X-ray study confirmed the trans-stereochemistry around the cyclopropyl ring. Use of 5 in Suzuki reactions, with a variety of aryl or heteroaryl coupling partners, provided trans-2-(trifluoromethyl)cyclopropyl products in moderate to excellent yields (17-90%).

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Year:  2013        PMID： 23952128     DOI： 10.1021/ol401636d

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


  3 in total

1.  Highly Diastereo- and Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes via Myoglobin-Catalyzed Transfer of Trifluoromethylcarbene.

Authors:  Antonio Tinoco; Viktoria Steck; Vikas Tyagi; Rudi Fasan
Journal:  J Am Chem Soc       Date:  2017-04-10       Impact factor: 15.419

2.  Divergent Synthesis of Cyclopropane-Containing Lead-Like Compounds, Fragments and Building Blocks through a Cobalt Catalyzed Cyclopropanation of Phenyl Vinyl Sulfide.

Authors:  Stephen J Chawner; Manuel J Cases-Thomas; James A Bull
Journal:  European J Org Chem       Date:  2017-09-11

3.  Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates.

Authors:  Julia Altarejos; David Sucunza; Juan J Vaquero; Javier Carreras
Journal:  Org Lett       Date:  2021-07-28       Impact factor: 6.005
  3 in total

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