Literature DB >> 14986960

Practical preparation of N-(1-Alkynyl)sulfonamides and their remote diastereoselective addition to aldehydes via titanation.

Shuji Hirano1, Ryoichi Tanaka, Hirokazu Urabe, Fumie Sato.   

Abstract

Aliphatic and aromatic sulfonamides were alkynylated with 1-bromo-1-alkynes in the catalytic presence of CuI to give N-(1-alkynyl)sulfonamides in good to excellent yields. The acetylene-titanium complexes generated from N-(1-alkynyl)benzosultams underwent diastereoselective addition to aldehydes. [reaction: see text]

Entities:  

Year:  2004        PMID： 14986960     DOI： 10.1021/ol036396b

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


  6 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

3.  SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors:  Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal:  Organic Synth       Date:  2007

4.  Stereoselective synthesis of β-hydroxy enamines, aminocyclopropanes, and 1,3-amino alcohols via asymmetric catalysis.

Authors:  Petr Valenta; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

5.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

Review 6.  Preparation and Utility of N-Alkynyl Azoles in Synthesis.

Authors:  Brandon Reinus; Sean M Kerwin
Journal:  Molecules       Date:  2019-01-24       Impact factor: 4.411
  6 in total

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