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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 7
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Original Articles

N-Alkylation of Amino Acid Esters Using Sodium Triacetoxyborohydride

Joshi M. Ramanjulu Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104–6323
&
Madeleine M. Joullié Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104–6323
Pages 1379-1384 | Received 04 Oct 1995, Published online: 15 Aug 2006

Citations (23)

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BruceA. Davis & DavidA. Durden. (2000) Reductive Methylation of Secondary Amines Containing Reducible, Hydrolyzable and Sterically Hindered Groups. Synthetic Communications 30:18, pages 3353-3362.
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Articles from other publishers (22)

Charlotte E. Coomber & Louis J. Diorazio. (2022) N ‐Alkylation of α‐Amino Esters and Amides through Hydrogen Borrowing . European Journal of Organic Chemistry 2022:32.
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Tao Yan, Ben L. Feringa & Katalin Barta. (2021) Direct Catalytic N ‐Alkylation of α‐Amino Acid Esters and Amides Using Alcohols with High Retention of Stereochemistry . ChemSusChem 14:11, pages 2303-2307.
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A.F. Abdel-Magid. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 85 150 .
Santimukul Santra & J. Manuel Perez. (2011) Selective N -Alkylation of β-Alanine Facilitates the Synthesis of a Poly(amino acid)-Based Theranostic Nanoagent . Biomacromolecules 12:11, pages 3917-3927.
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Emilia Lucia Belsito, Rosaria De Marco, Maria Luisa Di Gioia, Angelo Liguori, Francesca Perri & Maria Caterina Viscomi. (2010) N-(4-Nitrophenylsulfonyl)- and N-(Fluorenylmethoxycarbonyl)-N-ethyl Amino Acid Methyl Esters - A Practical Approach. European Journal of Organic Chemistry 2010:22, pages 4245-4252.
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Luigi Aurelio & Andrew B. Hughes. 2009. Amino Acids, Peptides and Proteins in Organic Chemistry. Amino Acids, Peptides and Proteins in Organic Chemistry 245 289 .
S. Goreti Silva, J. Enrique Rodríguez-Borges, Eduardo F. Marques & M. Luísa C. do Vale. (2009) Towards novel efficient monomeric surfactants based on serine, tyrosine and 4-hydroxyproline: synthesis and micellization properties. Tetrahedron 65:21, pages 4156-4164.
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Yunyun Yuan, Gang Liu, Li, Zhanguo Wang & Lin Wang. (2006) Synthesis of Diverse Benzo[1,4]oxazin-3-one-Based Compounds Using 1,5-Difluoro-2,4-dinitrobenzene. Journal of Combinatorial Chemistry 9:1, pages 158-170.
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Ahmed F. Abdel-MagidSteven J. Mehrman. (2006) A Review on the Use of Sodium Triacetoxyborohydride in the Reductive Amination of Ketones and Aldehydes. Organic Process Research & Development 10:5, pages 971-1031.
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Duke M. Fitch, Karen A. Evans, Deping Chai & Kevin J. Duffy. (2005) A Highly Efficient, Asymmetric Synthesis of Benzothiadiazine-Substituted Tetramic Acids:  Potent Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase. Organic Letters 7:24, pages 5521-5524.
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Eric Biron & Horst Kessler. (2005) Convenient Synthesis of N -Methylamino Acids Compatible with Fmoc Solid-Phase Peptide Synthesis . The Journal of Organic Chemistry 70:13, pages 5183-5189.
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Tomoyasu Hirose, Toshiaki Sunazuka, Daisuke Yamamoto, Naoto Kojima, Tatsuya Shirahata, Yoshihiro Harigaya, Isao Kuwajima & Satoshi Ōmura. (2005) Determination of the absolute stereochemistry and asymmetric total synthesis of madindolines A and B: a practical improvement to a second-generation approach from the first-generation. Tetrahedron 61:25, pages 6015-6039.
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Luigi Aurelio, Robert T. C. Brownlee & Andrew B. Hughes. (2004) Synthetic Preparation of N -Methyl-α-amino Acids . Chemical Reviews 104:12, pages 5823-5846.
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Anneke HacklingRobin GhoshSylvie PerachonAndré MannHans-Dieter HöltjeCamille G. WermuthJean-Charles SchwartzWolfgang SipplPierre SokoloffHolger Stark. (2003) N -(ω-(4-(2-Methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as Dopamine D 2 and D 3 Receptor Ligands . Journal of Medicinal Chemistry 46:18, pages 3883-3899.
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Tomoyasu Hirose, Toshiaki Sunazuka, Tatsuya Shirahata, Daisuke Yamamoto, Yoshihiro Harigaya, Isao Kuwajima & Satoshi Ōmura. (2002) Short Total Synthesis of (+)-Madindolines A and B. Organic Letters 4:4, pages 501-503.
Crossref
Ellen W. Baxter & Allen B. Reitz. 2004. Organic Reactions. Organic Reactions 1 714 .
Chit ThanHiromi MorimotoPhilip G. WilliamsKareem A. H. ChehadeDouglas A. AndresH. Peter Spielmann. (2001) Preparation, NMR Characterization, and Labeling Reactions of Tritiated Triacetoxy Sodium Borohydride. The Journal of Organic Chemistry 66:10, pages 3602-3605.
Crossref
Joshi M. Ramanjulu, Madeleine M. Joullié & Wen‐Ren Li. (2013) Synthetic Studies of a Didemnin B Analog Based on a 2,3‐Diamino Sugar Scaffolding. Journal of the Chinese Chemical Society 48:1, pages 1-4.
Crossref
Thomas Rückle, Benoit Dubray, Francis Hubler & Manfred Mutter. (1999) Efficient one-pot synthesis of N-ethyl amino acids. Journal of Peptide Science 5:1, pages 56-58.
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Jason J. Chruma, Dalibor Sames & Robin Polt. (1997) General method for the synthesis of N-methyl amino acids and N-alkyl amino esters from O'Donnell's Schiff bases. Tetrahedron Letters 38:29, pages 5085-5086.
Crossref
Mui Mui Sim & Arasu Ganesan. (1997) Solution-Phase Synthesis of a Combinatorial Thiohydantoin Library 1 . The Journal of Organic Chemistry 62:10, pages 3230-3235.
Crossref
J. M. RAMANJULU & M. M. JOULLIE. (2010) ChemInform Abstract: N‐Alkylation of Amino Acid Esters Using Sodium Triacetoxyborohydride.. ChemInform 27:31.
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