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Literature DB >> 20066026

Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

Patrick G McGarraugh¹, Stacey E Brenner.

Abstract

A new bifunctional organocatalyst with a novel structural and functional motif has been developed. This bifunctional sulfonamide organocatalyst was used in the conjugate addition of 1,3-dicarbonyl compounds (13) to β-nitrostyrenes (12). Yields up to 91% and enantiomeric excesses up to 79% were obtained in this reaction. This catalyst activates both 13 via its basic moiety and 12 through hydrogen bonding.

Entities: Chemical Species

Year: 2009 PMID： 20066026 PMCID： PMC2659672 DOI： 10.1016/j.tet.2008.11.027

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

35 in total

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Journal: Org Lett Date: 2005-05-12 Impact factor: 6.005

2. Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance.

Authors: Séamus H McCooey; Stephen J Connon
Journal: Angew Chem Int Ed Engl Date: 2005-10-07 Impact factor: 15.336

3. Catalytic enantioselective synthesis of flavanones and chromanones.

Authors: Margaret M Biddle; Michael Lin; Karl A Scheidt
Journal: J Am Chem Soc Date: 2007-03-10 Impact factor: 15.419

4. Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst--synthesis of optically active tetrahydro-beta-carbolines.

Authors: Wei Zhuang; Rita G Hazell; Karl Anker Jørgensen
Journal: Org Biomol Chem Date: 2005-06-21 Impact factor: 3.876

5. Chiral binaphthyl-derived amine-thiourea organocatalyst-promoted asymmetric Morita-Baylis-Hillman reaction.

Authors: Jian Wang; Hao Li; Xinhong Yu; Liansuo Zu; Wei Wang
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

6. Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction.

Authors: Katsuya Matsui; Shinobu Takizawa; Hiroaki Sasai
Journal: J Am Chem Soc Date: 2005-03-23 Impact factor: 15.419

7. A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions.

Authors: Wei Zhuang; Thomas B Poulsen; Karl Anker Jørgensen
Journal: Org Biomol Chem Date: 2005-07-27 Impact factor: 3.876

8. Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea.

Authors: Tomotaka Okino; Yasutaka Hoashi; Tomihiro Furukawa; Xuenong Xu; Yoshiji Takemoto
Journal: J Am Chem Soc Date: 2005-01-12 Impact factor: 15.419

9. Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction.

Authors: Kazuaki Ishihara; Yuji Kosugi; Shuhei Umemura; Akira Sakakura
Journal: Org Lett Date: 2008-06-27 Impact factor: 6.005

10. Enantioselective, organocatalytic oxy-michael addition to gamma/delta-hydroxy-alpha,beta-enones: boronate-amine complexes as chiral hydroxide synthons.

Authors: De Run Li; Andiappan Murugan; J R Falck
Journal: J Am Chem Soc Date: 2007-12-13 Impact factor: 15.419

2 in total

1. Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts.

Authors: Yunus E Türkmen; Viresh H Rawal
Journal: J Org Chem Date: 2013-08-14 Impact factor: 4.354

Review 2. Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors: Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal: Molecules Date: 2020-01-18 Impact factor: 4.411

2 in total