Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Literature DB >> 20809579

N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Eric M Phillips¹, Matthias Riedrich, Karl A Scheidt.

Abstract

An efficient intermolecular conjugate addition of alcohols to activated alkenes catalyzed by N-heterocyclic carbenes has been developed. With 5 mol % of the free carbene derived from IMes·HCl, unsaturated ketones and esters are competent substrates, and a variety of primary and secondary alcohols can be employed as the nucleophile. No oligomerization is observed under these mild conditions for effective hydroalkoxylation. In addition to reactions with activated alkenes, IMes catalyzes the formation of vinyl ethers through the 1,4-addition of alcohols to ynones and promotes tandem conjugate addition/Michael cascade reactions. Preliminary data support a Brønsted base mechanism with the free carbene.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2010 PMID： 20809579 PMCID： PMC2944903 DOI： 10.1021/ja1061196

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

30 in total

1. Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors: Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal: Aldrichimica Acta Date: 2009 Impact factor: 3.667

2. Extending mechanistic routes in heterazolium catalysis--promising concepts for versatile synthetic methods.

Authors: Kirsten Zeitler
Journal: Angew Chem Int Ed Engl Date: 2005-11-25 Impact factor: 15.336

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

Authors: Mohammad Movassaghi; Michael A Schmidt
Journal: Org Lett Date: 2005-06-09 Impact factor: 6.005

4. Enantioselective organocatalytic domino oxa-Michael/aldol/hemiacetalization: synthesis of polysubstituted furofuranes containing four stereocenters.

Authors: Efraím Reyes; Garazi Talavera; Jose L Vicario; Dolores Badía; Luisa Carrillo
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

5. Basicity of a stable carbene, 1,3-di-tert-butylimidazol-2-ylidene, in THF.

Authors: Yeong-Joon Kim; Andrew Streitwieser
Journal: J Am Chem Soc Date: 2002-05-22 Impact factor: 15.419

6. P(RNCH(2)CH(2))(3)N: efficient 1,4-addition catalysts.

Authors: Philip B Kisanga; Palanichamy Ilankumaran; Brandon M Fetterly; John G Verkade
Journal: J Org Chem Date: 2002-05-31 Impact factor: 4.354

7. N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors: Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal: J Am Chem Soc Date: 2009-12-23 Impact factor: 15.419

8. Highly diastereoselective oxy-Michael additions of enantiopure delta-lactol anions to nitroalkenes: asymmetric synthesis of 1,2-amino alcohols.

Authors: Nicola J Adderley; David J Buchanan; Darren J Dixon; Dramane I Lainé
Journal: Angew Chem Int Ed Engl Date: 2003-09-15 Impact factor: 15.336

9. Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides.

Authors: Xin Xiong; Caroline Ovens; Adam W Pilling; John W Ward; Darren J Dixon
Journal: Org Lett Date: 2008-01-23 Impact factor: 6.005

10. N-heterocyclic carbene catalyzed aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines.

Authors: Lin He; Teng-Yue Jian; Song Ye
Journal: J Org Chem Date: 2007-08-18 Impact factor: 4.354

15 in total

Review 1. 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

2. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

3. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors: Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal: Chem Sci Date: 2014-05-01 Impact factor: 9.825

4. Metal-free catalytic enantioselective C-B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes.

Authors: Hao Wu; Suttipol Radomkit; Jeannette M O'Brien; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2012-05-04 Impact factor: 15.419

5. An N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones.

Authors: Julien Dugal-Tessier; Elizabeth A O'Bryan; Thomas B H Schroeder; Daniel T Cohen; Karl A Scheidt
Journal: Angew Chem Int Ed Engl Date: 2012-04-04 Impact factor: 15.336

6. Lewis acid activated synthesis of highly substituted cyclopentanes by the N-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters.

Authors: Daniel T Cohen; Benoit Cardinal-David; Karl A Scheidt
Journal: Angew Chem Int Ed Engl Date: 2011-01-14 Impact factor: 15.336