Literature DB >> 20521800

ROMP-derived oligomeric phosphates for application in facile benzylation.

Toby R Long1, Pradip K Maity, Thiwanka B Samarakoon, Paul R Hanson.   

Abstract

The development of new ROMP-based oligomeric benzyl phosphates (OBP(n)) is reported for use as soluble, stable benzylating reagents. These oligomeric reagents are readily synthesized from commercially available materials and conveniently polymerized and purified in a one-pot process, affording bench-stable, pure white, free-flowing solids on multigram scale. Utilization in benzylation reactions with a variety of nucleophiles is reported.

Entities:  

Mesh:

Substances:

Year:  2010        PMID: 20521800      PMCID: PMC2925234          DOI: 10.1021/ol1006604

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


  33 in total

1.  Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies.

Authors:  Dennis J. Gravert; Kim D. Janda
Journal:  Chem Rev       Date:  1997-04-01       Impact factor: 60.622

2.  Three-component synthesis of 1,4-diazepin-5-ones and the construction of gamma-turn-like peptidomimetic libraries.

Authors:  Erik Fenster; Dinesh K Rayabarapu; Mianji Zhang; Shubhasish Mukherjee; David Hill; Ben Neuenswander; Frank Schoenen; Paul R Hanson; Jeffrey Aubé
Journal:  J Comb Chem       Date:  2008-02-07

3.  Functionalized Polymers-Emerging Versatile Tools for Solution-Phase Chemistry and Automated Parallel Synthesis.

Authors:  Andreas Kirschning; Holger Monenschein; Rüdiger Wittenberg
Journal:  Angew Chem Int Ed Engl       Date:  2001-02-16       Impact factor: 15.336

4.  Dendritic aliphatic polyethers as high-loading soluble supports for carbonyl compounds and parallel membrane separation techniques.

Authors:  Rainer Haag; Alexander Sunder; André Hebel; Sebastian Roller
Journal:  J Comb Chem       Date:  2002 Mar-Apr

5.  Lewis acid-promoted Friedel-Crafts alkylation reactions with alpha-ketophosphate electrophiles.

Authors:  Austin G Smith; Jeffrey S Johnson
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

6.  Oligomeric benzylsulfonium salts: facile benzylation via high-load ROMP reagents.

Authors:  Mianji Zhang; Daniel L Flynn; Paul R Hanson
Journal:  J Org Chem       Date:  2007-04-04       Impact factor: 4.354

7.  Soluble polymer-supported organic synthesis.

Authors:  P H Toy; K D Janda
Journal:  Acc Chem Res       Date:  2000-08       Impact factor: 22.384

8.  Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations.

Authors:  Kerry E Murphy; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419

9.  A reductive cyclization approach to attenol A.

Authors:  Thomas E La Cruz; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2007-03-09       Impact factor: 4.354

10.  Parallel synthesis of terminal alkynes using a ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate.

Authors:  Anthony G M Barrett; Brian T Hopkins; Andrew C Love; Livio Tedeschi
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005

View more
  10 in total

1.  Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol.

Authors:  Naeem Asad; Paul R Hanson; Toby R Long; Dinesh K Rayabarapu; Alan Rolfe
Journal:  Chem Commun (Camb)       Date:  2011-07-05       Impact factor: 6.222

2.  Facile (triazolyl)methylation of MACOS-derived benzofused sultams utilizing ROMP-derived OTP reagents.

Authors:  Saqib Faisal; Farman Ullah; Pradip K Maity; Alan Rolfe; Thiwanka B Samarakoon; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-03-05       Impact factor: 3.784

3.  Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents.

Authors:  Pradip K Maity; Saqib Faisal; Alan Rolfe; Diana Stoianova; Paul R Hanson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

4.  Monomer-on-monomer (MoM) Mitsunobu reaction: facile purification utilizing surface-initiated sequestration.

Authors:  Pradip K Maity; Alan Rolfe; Thiwanka B Samarakoon; Saqib Faisal; Ryan D Kurtz; Toby R Long; Alexander Schätz; Daniel L Flynn; Robert N Grass; Wendelin J Stark; Oliver Reiser; Paul R Hanson
Journal:  Org Lett       Date:  2010-12-01       Impact factor: 6.005

5.  High-load, hybrid Si-ROMP reagents.

Authors:  Alan Rolfe; Joanna K Loh; Pradip K Maity; Paul R Hanson
Journal:  Org Lett       Date:  2010-12-01       Impact factor: 6.005

6.  "Click"-capture, ring-opening metathesis polymerization (ROMP), release: facile triazolation utilizing ROMP-derived oligomeric phosphates.

Authors:  Toby R Long; Saqib Faisal; Pradip K Maity; Alan Rolfe; Ryan Kurtz; Sarra V Klimberg; Muhammad-Rabbie Najjar; Fatima Z Basha; Paul R Hanson
Journal:  Org Lett       Date:  2011-03-24       Impact factor: 6.005

7.  Benzylmorpholine analogs as selective inhibitors of lung cytochrome P450 2A13 for the chemoprevention of lung cancer in tobacco users.

Authors:  Linda C Blake; Anuradha Roy; David Neul; Frank J Schoenen; Jeffrey Aubé; Emily E Scott
Journal:  Pharm Res       Date:  2013-06-12       Impact factor: 4.200

8.  Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Alan Rolfe; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

9.  Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Thiwanka B Samarakoon; Robert L Sourk; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

10.  Himic Anhydride: A Retro Diels-Alder Reaction for the Organic Laboratory and an Accompanying NMR Study.

Authors:  Lee T Birchall; Sara Shehata; Christopher J Serpell; Ewan R Clark; Stefano C G Biagini
Journal:  J Chem Educ       Date:  2021-11-24       Impact factor: 2.979

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.