Literature DB >> 17559219

Preparation and use of enantioenriched allenylsilanes for the stereoselective synthesis of homopropargylic ethers.

Ryan A Brawn1, James S Panek.   

Abstract

A convenient procedure for the synthesis of highly enantioenriched allenylsilanes by Johnson orthoester Claisen rearrangement of 1-silyl propargylic alcohols is described. Allenylsilanes are then used as carbon nucleophiles in three-component, Lewis acid mediated additions to in situ generated oxonium ions, resulting in enantioenriched homopropargylic ethers.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17559219     DOI： 10.1021/ol070936d

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


  13 in total

1.  Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors:  David S Barnett; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

2.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

3.  C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Authors:  Tao Liang; Sang Kook Woo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

4.  Stereoselective C-glycosidations with achiral and enantioenriched allenylsilanes.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

5.  Annulations of enantioenriched allenylsilanes with in situ generated iminium ions: stereoselective synthesis of diverse heterocycles.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

6.  Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes.

Authors:  Ryan A Brawn; Morgan Welzel; Jason T Lowe; James S Panek
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

7.  Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

8.  Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.

Authors:  Andy S Tsai; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-13       Impact factor: 6.005

9.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.

Authors:  Brett R Ambler; Sang Kook Woo; Michael J Krische
Journal:  ChemCatChem       Date:  2018-08-07       Impact factor: 5.686

10.  Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.