Literature DB >> 12354018

Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines.

Xiao-Long Qiu1, Feng-Ling Qing.   

Abstract

A short, efficient, and diastereomerically pure synthesis of N-Boc-cis-4-trifluoromethyl-L-proline (7) and N-Boc-cis-4-difluoromethyl-L-proline (9) from N-Boc-4-oxo-L-proline (4) is described. The reaction of 4 with Me(3)SiCF(3) and the conversion of the carbonyl group of 4 into the difluoromethylene group are the key steps for the synthesis of 7 and 9, respectively.

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Year:  2002        PMID： 12354018     DOI： 10.1021/jo0257400

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


  7 in total

1.  Design and synthesis of simplified taxol analogs based on the T-Taxol bioactive conformation.

Authors:  Jielu Zhao; Susan Bane; James P Snyder; Haipeng Hu; Kamalika Mukherjee; Carla Slebodnick; David G I Kingston
Journal:  Bioorg Med Chem       Date:  2011-10-13       Impact factor: 3.641

2.  Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates.

Authors:  Brett R Ambler; Ryan A Altman
Journal:  Org Lett       Date:  2013-10-11       Impact factor: 6.005

3.  Spectroscopic and X-ray crystallographic evidence for electrostatic effects in 4-substituted cyclohexanone-derived hydrazones, imines, and corresponding salts.

Authors:  David J Dibble; Joseph W Ziller; K A Woerpel
Journal:  J Org Chem       Date:  2011-09-14       Impact factor: 4.354

4.  Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent.

Authors:  Yufan Liang; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-12       Impact factor: 15.336

5.  Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group.

Authors:  Yufan Liang; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2015-07-23       Impact factor: 15.419

6.  Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines.

Authors:  Jin-Shun Lin; Fu-Li Wang; Xiao-Yang Dong; Wei-Wei He; Yue Yuan; Su Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2017-03-23       Impact factor: 14.919

7.  Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones.

Authors:  Yupu Qiao; Tuda Si; Ming-Hsiu Yang; Ryan A Altman
Journal:  J Org Chem       Date:  2014-07-15       Impact factor: 4.354
  7 in total

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