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Literature DB >> 20369901

Enantioselective thiourea-catalyzed cationic polycyclizations.

Robert R Knowles¹, Song Lin, Eric N Jacobsen.

Abstract

A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation-pi interactions are a principal determinant of enantioselectivity.

Entities: Chemical

Mesh：

Substances：
Cations
Lactams
Thiourea

Year: 2010 PMID： 20369901 PMCID： PMC2989498 DOI： 10.1021/ja101256v

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

36 in total

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3. A new artificial cyclase for polyprenoids: enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione, and (-)-11'-deoxytaondiol methyl ether.

Authors: Hideaki Ishibashi; Kazuaki Ishihara; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2004-09-15 Impact factor: 15.419

4. Highly enantioselective catalytic acyl-pictet-spengler reactions.

Authors: Mark S Taylor; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2004-09-01 Impact factor: 15.419

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Authors: J D Dunitz
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6. A specific amino acid repeat in squalene and oxidosqualene cyclases.

Authors: K Poralla; A Hewelt; G D Prestwich; I Abe; I Reipen; G Sprenger
Journal: Trends Biochem Sci Date: 1994-04 Impact factor: 13.807

7. A new asymmetric synthesis of trans-hydroisoquinolones.

Authors: A Kamatani; L E Overman
Journal: Org Lett Date: 2001-04-19 Impact factor: 6.005

8. Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

Authors: Akira Sakakura; Atsushi Ukai; Kazuaki Ishihara
Journal: Nature Date: 2007-02-22 Impact factor: 49.962

9. Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors: Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal: J Am Chem Soc Date: 2006-03-22 Impact factor: 15.419

10. Lithium-cation/pi complexes of aromatic systems. The effect of increasing the number of fused rings.

Authors: Jean-François Gal; Pierre-Charles Maria; Michèle Decouzon; Otilia Mó; Manuel Yáñez; José Luis M Abboud
Journal: J Am Chem Soc Date: 2003-08-27 Impact factor: 15.419

62 in total

1. Attractive noncovalent interactions in asymmetric catalysis: links between enzymes and small molecule catalysts.

Authors: Robert R Knowles; Eric N Jacobsen
Journal: Proc Natl Acad Sci U S A Date: 2010-10-18 Impact factor: 11.205

2. Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors: Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal: J Am Chem Soc Date: 2013-09-11 Impact factor: 15.419

10. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Authors: Giulia Bergonzini; Corinna S Schindler; Carl-Johan Wallentin; Eric N Jacobsen; Corey R J Stephenson
Journal: Chem Sci Date: 2014-01 Impact factor: 9.825

Enantioselective thiourea-catalyzed cationic polycyclizations.

1. The Cationminus signpi Interaction.

2. Enzyme Mechanisms for Polycyclic Triterpene Formation.

3. A new artificial cyclase for polyprenoids: enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione, and (-)-11'-deoxytaondiol methyl ether.

4. Highly enantioselective catalytic acyl-pictet-spengler reactions.

Review 5. Win some, lose some: enthalpy-entropy compensation in weak intermolecular interactions.

6. A specific amino acid repeat in squalene and oxidosqualene cyclases.

7. A new asymmetric synthesis of trans-hydroisoquinolones.

8. Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

9. Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

10. Lithium-cation/pi complexes of aromatic systems. The effect of increasing the number of fused rings.

1. Attractive noncovalent interactions in asymmetric catalysis: links between enzymes and small molecule catalysts.

2. Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Review 3. Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution.

4. On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

5. Silanediol Anion Binding and Enantioselective Catalysis.

6. The progression of chiral anions from concepts to applications in asymmetric catalysis.

7. Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

8. Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

9. A Cyclization/Oxygenation Scheme for the Conversion of Polyenes into C3-Oxygenated Polycycles.

10. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.