Literature DB >> 24114116

Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.

Aaron Christopher1, Dahniel Brandes, Stephen Kelly, Thomas G Minehan.   

Abstract

Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted β-, γ-, and δ-lactones in good to excellent yields.

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Year:  2013        PMID： 24114116      PMCID： PMC3845887          DOI： 10.1039/c3ob41777h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  11 in total

Review 1.  Recent developments in ring opening polymerization of lactones for biomedical applications.

Authors:  Ann-Christine Albertsson; Indra K Varma
Journal:  Biomacromolecules       Date:  2003 Nov-Dec       Impact factor: 6.988

2.  Catalytic asymmetric assembly of stereodefined propionate units: an enantioselective total synthesis of (-)-pironetin.

Authors:  Xiaoqiang Shen; Andrew S Wasmuth; Junping Zhao; Cheng Zhu; Scott G Nelson
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

3.  Low-temperature n-butyllithium-induced rearrangement of allyl 1,1-dichlorovinyl ethers.

Authors:  Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas Minehan
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

4.  α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines.

Authors:  Jared W Rigoli; Sara A Moyer; Simon D Pearce; Jennifer M Schomaker
Journal:  Org Biomol Chem       Date:  2012-01-20       Impact factor: 3.876

5.  A de novo enantioselective total synthesis of (-)-laulimalide.

Authors:  Scott G Nelson; Wing S Cheung; Andrew J Kassick; Mark A Hilfiker
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

6.  A Highly Diastereoselective, Tandem Mukaiyama Aldol-Lactonization Route to beta-Lactones: Application to a Concise Synthesis of the Potent Pancreatic Lipase Inhibitor, (-)-Panclicin D.

Authors:  Hong Woon Yang; Daniel Romo
Journal:  J Org Chem       Date:  1997-01-10       Impact factor: 4.354

7.  [3,3]-Sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: synthesis of substituted 2-indanones and indenes.

Authors:  Armen A Tudjarian; Thomas G Minehan
Journal:  J Org Chem       Date:  2011-03-25       Impact factor: 4.354

8.  Practical, catalytic, asymmetric synthesis of beta-lactones via a sequential ketene dimerization/hydrogenation process: inhibitors of the thioesterase domain of fatty acid synthase.

Authors:  Vikram C Purohit; Robyn D Richardson; Jeffrey W Smith; Daniel Romo
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

9.  A simple stereocontrolled synthesis of salinosporamide A.

Authors:  Leleti Rajender Reddy; P Saravanan; E J Corey
Journal:  J Am Chem Soc       Date:  2004-05-26       Impact factor: 15.419

10.  Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers.

Authors:  Juan R Sosa; Armen A Tudjarian; Thomas G Minehan
Journal:  Org Lett       Date:  2008-10-11       Impact factor: 6.005
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