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Literature DB >> 26262944

Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.

Otome E Okoromoba¹, Gerald B Hammond¹, Bo Xu².

Abstract

DMPU/HF (HF content 65 wt %/wt) is an ideal nucleophilic fluorination reagent for the diastereoselective synthesis of substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines via a fluoro-Prins reaction. When compared to classical nucleophilic fluorination reagents like pyridine/HF, DMPU/HF gives both higher yields and better diastereoselectivity.

Entities: Chemical Disease Gene

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Year: 2015 PMID： 26262944 PMCID： PMC5381514 DOI： 10.1021/acs.orglett.5b01919

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

12 in total

1. Total synthesis of the marine toxin polycavernoside A via selective macrolactonization of a trihydroxy carboxylic acid.

Authors: J D White; P R Blakemore; C C Browder; J Hong; C M Lincoln; P A Nagornyy; L A Robarge; D J Wardrop
Journal: J Am Chem Soc Date: 2001-09-05 Impact factor: 15.419

2. Synthesis and structure revision of calyxin natural products.

Authors: Xia Tian; James J Jaber; Scott D Rychnovsky
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

3. Synthesis of (+)-spirolaxine methyl ether.

Authors: Raffaella Nannei; Sabrina Dallavalle; Lucio Merlini; Adriana Bava; Gianluca Nasini
Journal: J Org Chem Date: 2006-08-04 Impact factor: 4.354

4. Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking Prins with Cope and Grob.

Authors: Roger W Alder; Jeremy N Harvey; Mark T Oakley
Journal: J Am Chem Soc Date: 2002-05-08 Impact factor: 15.419

5. Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

Authors: J J Jaber; K Mitsui; S D Rychnovsky
Journal: J Org Chem Date: 2001-06-29 Impact factor: 4.354

6. Electrooxidative Inter- and Intramolecular Carbon-Carbon Bond Formation Using Organothio Groups as Electroauxiliaries.

Authors: Masanobu Sugawara; Masao Tatsumi; Naoki Kise
Journal: J Org Chem Date: 1998-08-21 Impact factor: 4.354

7. Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles.

Authors: Guillaume G Launay; Alexandra M Z Slawin; David O'Hagan
Journal: Beilstein J Org Chem Date: 2010-04-26 Impact factor: 2.883

Review 8. Understanding organofluorine chemistry. An introduction to the C-F bond.

Authors: David O'Hagan
Journal: Chem Soc Rev Date: 2007-10-17 Impact factor: 54.564

Review 9. Fluorine in pharmaceuticals: looking beyond intuition.

Authors: Klaus Müller; Christoph Faeh; François Diederich
Journal: Science Date: 2007-09-28 Impact factor: 47.728

10. Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Authors: Otome E Okoromoba; Junbin Han; Gerald B Hammond; Bo Xu
Journal: J Am Chem Soc Date: 2014-10-02 Impact factor: 15.419

13 in total

Review 1. Hydrogen Bonding: Regulator for Nucleophilic Fluorination.

Authors: Shengzong Liang; Gerald B Hammond; Bo Xu
Journal: Chemistry Date: 2017-10-05 Impact factor: 5.236

2. Bromofluorination of Unsaturated Compounds using DMPU/HF as a Fluorinating Reagent.

Authors: Shengzong Liang; Francis J Barrios; Otome E Okoromoba; Zofia Hetman; Bo Xu; Gerald B Hammond
Journal: J Fluor Chem Date: 2017-08-04 Impact factor: 2.050

3. Solventless and Metal-free Regioselective Hydrofluorination of Functionalized Alkynes and Allenes: An Efficient Protocol for the Synthesis of gem-Difluorides.

Authors: Zhichao Lu; Bhvandip S Bajwa; Shiwen Liu; Sheye Lee; Gerald B Hammond; Bo Xu
Journal: Green Chem Date: 2019-02-15 Impact factor: 10.182

Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.

1. Total synthesis of the marine toxin polycavernoside A via selective macrolactonization of a trihydroxy carboxylic acid.

2. Synthesis and structure revision of calyxin natural products.

3. Synthesis of (+)-spirolaxine methyl ether.

4. Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking Prins with Cope and Grob.

5. Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

6. Electrooxidative Inter- and Intramolecular Carbon-Carbon Bond Formation Using Organothio Groups as Electroauxiliaries.

7. Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles.

Review 8. Understanding organofluorine chemistry. An introduction to the C-F bond.

Review 9. Fluorine in pharmaceuticals: looking beyond intuition.

10. Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Review 1. Hydrogen Bonding: Regulator for Nucleophilic Fluorination.

2. Bromofluorination of Unsaturated Compounds using DMPU/HF as a Fluorinating Reagent.

3. Solventless and Metal-free Regioselective Hydrofluorination of Functionalized Alkynes and Allenes: An Efficient Protocol for the Synthesis of gem-Difluorides.

4. Multifaceted Ion Exchange Resin-Supported Hydrogen Fluoride: A Path to Flow Hydrofluorination.

5. A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.

6. Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

7. Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

8. HBr-DMPU: The First Aprotic Organic Solution of Hydrogen Bromide.

9. Widely Applicable Hydrofluorination of Alkenes via Bifunctional Activation of Hydrogen Fluoride.

10. Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.