Literature DB >> 22844160

A One-Pot Selective Synthesis of N-Boc Protected Secondary Amines: Tandem Direct Reductive Amination/N-Boc Protection.

Raghupathi Neelarapu1, Pavel A Petukhov.   

Abstract

A one-pot tandem direct reductive amination of aldehydes with primary amines resulting in N-Boc secondary amines using a (Boc)(2)O/sodium triacetoxyborohydride (STAB) system is reported. The tandem procedure is efficient, selective, and versatile, giving excellent yields of N-Boc protected secondary amines even in those cases where the products are prone to intramolecular lactamization.

Entities:  

Year:  2012        PMID： 22844160      PMCID： PMC3404846          DOI： 10.1016/j.tet.2012.06.055

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  12 in total

1.  Reductive and catalytic monoalkylation of primary amines using nitriles as an alkylating reagent.

Authors:  Hironao Sajiki; Takashi Ikawa; Kosaku Hirota
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

2.  Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

Authors:  Ahmed F. Abdel-Magid; Kenneth G. Carson; Bruce D. Harris; Cynthia A. Maryanoff; Rekha D. Shah
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

Review 3.  Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug.

Authors:  Paul A Marks; Ronald Breslow
Journal:  Nat Biotechnol       Date:  2007-01       Impact factor: 54.908

4.  Remote control of diastereoselectivity in intramolecular reactions of chiral allylsilanes.

Authors:  Weston R Judd; Sooho Ban; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2006-10-25       Impact factor: 15.419

5.  Application of chemical cytochrome P-450 model systems to studies on drug metabolism. IV. Mechanism of piperidine metabolism pathways via an iminium intermediate.

Authors:  H Masumoto; S Ohta; M Hirobe
Journal:  Drug Metab Dispos       Date:  1991 Jul-Aug       Impact factor: 3.922

6.  Design, synthesis, docking, and biological evaluation of novel diazide-containing isoxazole- and pyrazole-based histone deacetylase probes.

Authors:  Raghupathi Neelarapu; Denise L Holzle; Subash Velaparthi; He Bai; Michael Brunsteiner; Sylvie Y Blond; Pavel A Petukhov
Journal:  J Med Chem       Date:  2011-06-02       Impact factor: 7.446

7.  Zn-alkynylide additions to acyl iminiums.

Authors:  Christian Fischer; Erick M Carreira
Journal:  Org Lett       Date:  2004-04-29       Impact factor: 6.005

8.  Efficient synthesis of gamma-lactams by a tandem reductive amination/lactamization sequence.

Authors:  Julica Nöth; Kevin J Frankowski; Benjamin Neuenswander; Jeffrey Aubé; Oliver Reiser
Journal:  J Comb Chem       Date:  2008-03-14

9.  Copper-catalyzed coupling of imines, acid chlorides, and alkynes: a multicomponent route to propargylamides.

Authors:  Daniel A Black; Bruce A Arndtsen
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005

10.  A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates.

Authors:  Erwan Le Gall; Antoine Pignon; Thierry Martens
Journal:  Beilstein J Org Chem       Date:  2011-07-20       Impact factor: 2.883
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  2 in total

1.  Design, Synthesis, Molecular Modeling, and Biological Evaluation of Novel Amine-based Histone Deacetylase Inhibitors.

Authors:  Hazem Abdelkarim; Raghupathi Neelarapu; Antonett Madriaga; Aditya S Vaidya; Irida Kastrati; Bhargava Karumudi; Yue-Ting Wang; Taha Y Taha; Gregory R J Thatcher; Jonna Frasor; Pavel A Petukhov
Journal:  ChemMedChem       Date:  2017-11-30       Impact factor: 3.466

2.  Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride.

Authors:  Nathaniel George; Samuel Ofori; Sean Parkin; Samuel G Awuah
Journal:  RSC Adv       Date:  2020-06-23       Impact factor: 4.036
  2 in total

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