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Literature DB >> 15932221

N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols.

Mohammad Movassaghi¹, Michael A Schmidt.

Abstract

[reaction: see text] A catalytic amidation of unactivated esters with amino alcohols is described. A series of solution studies in addition to the first X-ray structure of a carbene-alcohol complex support a carbene-base nucleophile activation mechanism.

Entities: Chemical Disease

Year: 2005 PMID： 15932221 DOI： 10.1021/ol050773y

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

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Cited

21 in total

Review 1. Carbene catalysts.

Authors: Jennifer L Moore; Tomislav Rovis
Journal: Top Curr Chem Date: 2010

2. Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

Authors: Harit U Vora; Tomislav Rovis
Journal: J Am Chem Soc Date: 2007-10-11 Impact factor: 15.419

Review 3. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors: Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal: Chem Rev Date: 2015-05-20 Impact factor: 60.622

4. Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

Authors: Peng Zhou; Wen-Juan Hao; Jin-Peng Zhang; Bo Jiang; Guigen Li; Shu-Jiang Tu
Journal: Chem Commun (Camb) Date: 2015-08-21 Impact factor: 6.222

5. Biosynthetic analysis of the petrobactin siderophore pathway from Bacillus anthracis.

Authors: Jung Yeop Lee; Brian K Janes; Karla D Passalacqua; Brian F Pfleger; Nicholas H Bergman; Haichuan Liu; Kristina Håkansson; Ravindranadh V Somu; Courtney C Aldrich; Stephen Cendrowski; Philip C Hanna; David H Sherman
Journal: J Bacteriol Date: 2006-12-22 Impact factor: 3.490

6. Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors: Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal: ACS Catal Date: 2012-02-29 Impact factor: 13.084

N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols.

Review 1. Carbene catalysts.

2. Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

Review 3. Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

4. Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

5. Biosynthetic analysis of the petrobactin siderophore pathway from Bacillus anthracis.

6. Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

7. Fusarisetin A: Scalable Total Synthesis and Related Studies.

8. Acyl transfer catalysis with 1,2,4-triazole anion.

9. Rearrangement of biaryl monoaminocarbenes via concerted asynchronous insertion into aromatic C-H bonds.

10. Catalytic amide formation with alpha'-hydroxyenones as acylating reagents.