Literature DB >> 28435948

Diversification reactions of γ-silyl allenyl esters: selective conversion to all-carbon quaternary centers and γ-allene dicarbinols.

Susovan Jana1, Animesh Roy, Salvatore D Lepore.   

Abstract

The unique reactivity of γ-silyl allenyl esters is described. Taking advantage of the silyl group as a fluoride acceptor, these allenoates readily underwent addition to a variety of electrophiles to selectively yield products with all-carbon quaternary centers or allenoate dicarbinols. These dicarbinols were subsequently converted to novel highly substituted 6-hydro-2-pyrones.

Entities:  

Year:  2017        PMID： 28435948      PMCID： PMC5510162          DOI： 10.1039/c7cc01708a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  19 in total

1.  Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources: Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one.

Authors:  Daniel Dobler; Oliver Reiser
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 2.  Allenes in catalytic asymmetric synthesis and natural product syntheses.

Authors:  Shichao Yu; Shengming Ma
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-23       Impact factor: 15.336

3.  Alpha-chiral acetylenes having an all-carbon quaternary center: phase transfer catalyzed enantioselective alpha alkylation of alpha-alkyl-alpha-alkynyl esters.

Authors:  Takuya Hashimoto; Kazuki Sakata; Keiji Maruoka
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Single-Flask Multicomponent Synthesis of Highly Substituted α-Pyrones via a Sequential Enolate Arylation and Alkenylation Strategy.

Authors:  Michael Grigalunas; Olaf Wiest; Paul Helquist
Journal:  Org Lett       Date:  2016-10-21       Impact factor: 6.005

5.  Palladium-catalyzed divergent reactions of α-diazocarbonyl compounds with allylic esters: construction of quaternary carbon centers.

Authors:  Zi-Sheng Chen; Xin-Hua Duan; Ping-Xin Zhou; Shaukat Ali; Jian-Yi Luo; Yong-Min Liang
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-23       Impact factor: 15.336

6.  Enhanced Nucleophilic Fluorination and Radiofluorination of Organosilanes Appended with Potassium-Chelating Leaving Groups.

Authors:  Mohammed H Al-Huniti; Shuiyu Lu; Victor W Pike; Salvatore D Lepore
Journal:  J Fluor Chem       Date:  2014-02-01       Impact factor: 2.050

7.  Anion-catalyzed addition of gamma-silylallenyl esters to aldehydes: a new entry into [3.2.1] bicyclic natural products.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

8.  Michael addition of allenoates to electron-deficient olefins: facile synthesis of 2-alkynyl-substituted glutaric acid derivatives.

Authors:  Le-Ping Liu; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2008-07-25       Impact factor: 6.005

9.  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

10.  Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration.

Authors:  Darius J Faizi; Adena Issaian; Ashlee J Davis; Suzanne A Blum
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419
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  1 in total

1.  Allenoate Prenucleophiles: A Triply Diastereoselective Approach to β-Hydroxy Esters Containing All-Carbon α-Quaternary Centers.

Authors:  Samantha L Maki; Pradip Maity; Shannon Dougherty; Jennifer Johns; Salvatore D Lepore
Journal:  Org Lett       Date:  2019-09-16       Impact factor: 6.072
  1 in total

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