Literature DB >> 20161309

Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

Tsung-Hao Fu1, Amy Bonaparte, Stephen F Martin.   

Abstract

A variety of heterocyclic alcohols and acetates were coupled with silyl ketene acetals and other π-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array of substituted β-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the π-nucleophile bears a chiral auxiliary.

Entities:  

Year:  2009        PMID： 20161309      PMCID： PMC2699308          DOI： 10.1016/j.tetlet.2009.02.018

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

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2.  Asymmetric Brønsted acid catalysis: enantioselective nucleophilic substitutions and 1,4-additions.

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3.  A new, non-iterative asymmetric synthesis of long-chain 1,3-polyols.

Authors:  M E Schwenter; P Vogel
Journal:  Chemistry       Date:  2000-11-17       Impact factor: 5.236

4.  Rapid synthesis of the N-methylwelwitindolinone skeleton.

Authors:  James A MacKay; Raynauld L Bishop; Viresh H Rawal
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

5.  Sequential one-pot InBr(3)-catalyzed 1,4- then 1,2-nucleophilic addition to enones.

Authors:  Marco Bandini; Pier Giorgio Cozzi; Massimo Giacomini; Paolo Melchiorre; Simona Selva; Achille Umani-Ronchi
Journal:  J Org Chem       Date:  2002-05-31       Impact factor: 4.354

6.  Calix[2]bipyrrole[2]furan and calix[2]bipyrrole[2]thiophene: new pyrrolic receptors exhibiting a preference for carboxylate anions.

Authors:  Jonathan L Sessler; Deqiang An; Won-Seob Cho; Vincent Lynch
Journal:  J Am Chem Soc       Date:  2003-11-12       Impact factor: 15.419

7.  Dependence of enantioselectivity on the ligand/metal ratio in the asymmetric Michael addition of indole to benzylidene malonates: electronic influence of substrates.

Authors:  Alexander Schätz; Ramesh Rasappan; Markus Hager; Anja Gissibl; Oliver Reiser
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  The Michael addition of indoles to alpha,beta-unsaturated ketones catalyzed by CeCl3.7H2O-NaI combination supported on silica gel.

Authors:  Giuseppe Bartoli; Massimo Bartolacci; Marcella Bosco; Gioia Foglia; Arianna Giuliani; Enrico Marcantoni; Letizia Sambri; Elisabetta Torregiani
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

9.  Asymmetric Friedel-Crafts alkylation of indoles with methyl (E)-2-oxo-4-aryl-3-butenoates catalyzed by Sc(OTf)3/pybox.

Authors:  Giovanni Desimoni; Giuseppe Faita; Marco Toscanini; Massimo Boiocchi
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Highly enantioselective Friedel-Crafts reaction of indoles with 2-enoylpyridine 1-oxides catalyzed by chiral pyridine 2,6-bis(5',5'-diphenyloxazoline)-Cu(II) complexes.

Authors:  Pradeep K Singh; Vinod K Singh
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005
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  7 in total

1.  Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core.

Authors:  Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

2.  Total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Vikram Bhat; Kevin M Allan; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-03-29       Impact factor: 15.419

3.  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Authors:  Paul A Allegretti; Khoi Huynh; Tarik J Ozumerzifon; Eric M Ferreira
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

4.  Formal syntheses of naturally occurring welwitindolinones.

Authors:  Tsung-hao Fu; William T McElroy; Mariam Shamszad; Stephen F Martin
Journal:  Org Lett       Date:  2012-07-25       Impact factor: 6.005

5.  Concise total synthesis of (±)-actinophyllic acid.

Authors:  Brett A Granger; Ivan T Jewett; Jeffrey D Butler; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

6.  Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.

Authors:  Tsung-Hao Fu; William T McElroy; Mariam Shamszad; Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

7.  Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes.

Authors:  Jie Ouyang; Rajat Maji; Markus Leutzsch; Benjamin Mitschke; Benjamin List
Journal:  J Am Chem Soc       Date:  2022-05-06       Impact factor: 16.383
  7 in total

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