Literature DB >> 27182091

Optimized Synthesis of a Pentafluoro-gem-diol and Conversion to a CF2Br-Glucopyranose through Trifluoroacetate-Release and Halogenation.

Robert A Hazlitt1, Jinu P John2, Que-Lynn Tran3, David A Colby1.   

Abstract

Pentafluoro-gem-diols are substrates that enable the synthesis of valuable difluoromethylene-containing organic molecules through the release of trifluoroacetate. Currently, only one synthetic strategy is available to assemble these important precursors. Herein, two new synthetic strategies to a complex pentafluoro-gem-diol are compared to the existing route, and an improved synthetic route has completed. Moreover, the first synthesis of a CF2Br-glucopyranose was finished by a tandem trifluoroacetate-release halogenation/cyclization protocol.

Entities:  

Keywords:  aldol reaction; fluorine; glycoside; halogenation; pyranose

Year:  2016        PMID： 27182091      PMCID： PMC4863236          DOI： 10.1016/j.tetlet.2016.03.064

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

Review 1.  Natural products as sources of new drugs over the 30 years from 1981 to 2010.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2012-02-08       Impact factor: 4.050

2.  Catalytic asymmetric fluorination comes of age.

Authors:  Vincent A Brunet; David O'Hagan
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  New selective haloform-type reaction yielding 3-hydroxy-2,2-difluoroacids: theoretical study of the mechanism.

Authors:  Santiago Olivella; Albert Solé; Oscar Jiménez; M Pilar Bosch; Angel Guerrero
Journal:  J Am Chem Soc       Date:  2005-03-02       Impact factor: 15.419

Review 4.  Synthetic methods for compounds having CF3-S units on carbon by trifluoromethylation, trifluoromethylthiolation, triflylation, and related reactions.

Authors:  Xiu-Hua Xu; Kohei Matsuzaki; Norio Shibata
Journal:  Chem Rev       Date:  2014-08-14       Impact factor: 60.622

5.  A new reagent for direct difluoromethylation.

Authors:  Yuta Fujiwara; Janice A Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Darryl D Dixon; Michael R Collins; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2012-01-13       Impact factor: 15.419

6.  Synthesis of α-halo-α,α-difluoromethyl ketones by a trifluoroacetate release/halogenation protocol.

Authors:  Jinu P John; David A Colby
Journal:  J Org Chem       Date:  2011-10-13       Impact factor: 4.354

7.  Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

Authors:  Shi-Liang Shi; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-04       Impact factor: 15.336

8.  3-deoxy-3,3-difluoro-D-arabinofuranose: first stereoselective synthesis and application in preparation of gem-difluorinated sugar nucleosides.

Authors:  Xingang Zhang; Hairong Xia; XiCheng Dong; Jing Jin; Wei-Dong Meng; Feng-Ling Qing
Journal:  J Org Chem       Date:  2003-11-14       Impact factor: 4.354

9.  An improved asymmetric reformatsky reaction mediated by (-)-N,N-dimethylaminoisoborneol.

Authors:  Ralf J Kloetzing; Tobias Thaler; Paul Knochel
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005

10.  Visible-light-induced direct C(sp3)-H difluromethylation of tetrahydroisoquinolines with the in situ generated difluoroenolates.

Authors:  Weipeng Li; Xuebin Zhu; Haibin Mao; Zhongkai Tang; Yixiang Cheng; Chengjian Zhu
Journal:  Chem Commun (Camb)       Date:  2014-07-18       Impact factor: 6.222
View more
  3 in total

1.  Conversion of Methyl Ketones and Methyl Sulfones into α-Deutero-α,α-Difluoromethyl Ketones and α-Deutero-α,α-Difluoromethyl Sulfones in Three Synthetic Steps.

Authors:  Munia F Sowaileh; Changho Han; Robert A Hazlitt; Eun Hoo Kim; Jinu P John; David A Colby
Journal:  Tetrahedron Lett       Date:  2016-12-21       Impact factor: 2.415

2.  Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones.

Authors:  Robert A Hazlitt; Que-Lynn Tran; Munia F Sowaileh; David A Colby
Journal:  J Org Chem       Date:  2017-01-31       Impact factor: 4.354

3.  Magnesium-Promoted Additions of Difluoroenolates to Unactivated Imines.

Authors:  Alex L Nguyen; Hari R Khatri; James R Woods; Cassidy S Baldwin; Frank R Fronczek; David A Colby
Journal:  J Org Chem       Date:  2018-02-27       Impact factor: 4.354
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.