Literature DB >> 28250502

Effect of Substituents and Stability of Transient Aluminum-Aminals in the Presence of Nucleophiles.

Francis J Barrios1, Brannon C Springer2, Robert A Hazlitt3, David A Colby3.   

Abstract

Disubstituted hydroxylamines were synthesized and used to form aluminum-amide complexes. These reagents masked carbonyl groups in situ from nucleophilic addition. The stability and utility of the aluminum-aminals are presented in the context of selectively controlling nucleophilic addition on substrates with multiple carbonyl groups.

Entities:  

Keywords:  aluminum; amides; amines; carbonyl complexes; nucleophilic addition

Year:  2014        PMID： 28250502      PMCID： PMC5328419          DOI： 10.1055/s-0034-1379635

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  13 in total

1.  Dialkylaluminum N,O-dimethylhydroxylamine complex as a reagent to mask reactive carbonyl groups in situ from nucleophiles.

Authors:  Francis J Barrios; Xuechao Zhang; David A Colby
Journal:  Org Lett       Date:  2010-11-01       Impact factor: 6.005

2.  Adsorption behavior of microbes on a QCM chip modified with an artificial siderophore-Fe3+ complex.

Authors:  Tomohiko Inomata; Hiroshi Eguchi; Yasuhiro Funahashi; Tomohiro Ozawa; Hideki Masuda
Journal:  Langmuir       Date:  2011-12-19       Impact factor: 3.882

3.  Synthetic approaches and total synthesis of natural zoapatanol.

Authors:  Catherine Taillier; Barbara Gille; Véronique Bellosta; Janine Cossy
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

4.  N-O chemistry for antibiotics: discovery of N-alkyl-N-(pyridin-2-yl)hydroxylamine scaffolds as selective antibacterial agents using nitroso Diels-Alder and ene chemistry.

Authors:  Timothy A Wencewicz; Baiyuan Yang; James R Rudloff; Allen G Oliver; Marvin J Miller
Journal:  J Med Chem       Date:  2011-09-15       Impact factor: 7.446

5.  Significance of hydrogen bonding at the S(1)' subsite of calpain I.

Authors:  I O Donkor; X Zheng; J Han; C Lacy; D D Miller
Journal:  Bioorg Med Chem Lett       Date:  2001-07-09       Impact factor: 2.823

6.  Methodology for in situ protection of aldehydes and ketones using trimethylsilyl trifluoromethanesulfonate and phosphines: selective alkylation and reduction of ketones, esters, amides, and nitriles.

Authors:  Kenzo Yahata; Masaki Minami; Yuki Yoshikawa; Kei Watanabe; Hiromichi Fujioka
Journal:  Chem Pharm Bull (Tokyo)       Date:  2013       Impact factor: 1.645

7.  Synthesis of omega-hydroxy ketones from omega-benzyloxy Weinreb amides by using a chemoselective nucleophilic addition/Birch reduction process.

Authors:  Catherine Taillier; Véronique Bellosta; Christophe Meyer; Janine Cossy
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

8.  o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen- and sulfur-containing substrates: scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections.

Authors:  K C Nicolaou; Casey J N Mathison; Tamsyn Montagnon
Journal:  J Am Chem Soc       Date:  2004-04-28       Impact factor: 15.419

9.  Step-economical access to valuable Weinreb amide 2,5-disubstituted pyrrolidines by a sequential one-pot two-directional cross-metathesis/cyclizing aza-Michael process.

Authors:  Hamza Boufroura; Marc Mauduit; Emmanuelle Drège; Delphine Joseph
Journal:  J Org Chem       Date:  2013-02-21       Impact factor: 4.354

10.  Control of transient aluminum-aminals for masking and unmasking reactive carbonyl groups.

Authors:  Francis J Barrios; Brannon C Springer; David A Colby
Journal:  Org Lett       Date:  2013-06-03       Impact factor: 6.005
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