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Literature DB >> 20568761

Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

Adam R Brown¹, Wen-Hsin Kuo, Eric N Jacobsen.

Abstract

Primary aminothiourea derivatives are shown to catalyze enantioselective alkylation of alpha-arylpriopionaldehdyes with diarylbromomethane. Evidence for a stepwise, S(N)1 mechanism in the substitution reaction induced by anion binding to the catalyst is provided by catalyst structure-activity studies, kinetic isotope effects, linear free-energy relationship studies, and competition experiments.

Entities: Chemical Gene Species

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Year: 2010 PMID： 20568761 PMCID： PMC2909636 DOI： 10.1021/ja103618r

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

27 in total

1. Titanium(IV)-catalyzed dynamic kinetic asymmetric transformation of alcohols, silyl ethers, and acetals under carbon allylation.

Authors: Manfred Braun; Wolfgang Kotter
Journal: Angew Chem Int Ed Engl Date: 2004-01-16 Impact factor: 15.336

2. 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

3. Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

Authors: Izzat T Raheem; Parvinder S Thiara; Emily A Peterson; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2007-10-17 Impact factor: 15.419

4. Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors: Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal: J Am Chem Soc Date: 2007-09-21 Impact factor: 15.419

Review 5. (Thio)urea organocatalysis--what can be learnt from anion recognition?

Authors: Zhiguo Zhang; Peter R Schreiner
Journal: Chem Soc Rev Date: 2009-02-18 Impact factor: 54.564

6. Light in aminocatalysis: the asymmetric intermolecular alpha-alkylation of aldehydes.

Authors: Paolo Melchiorre
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. anti-Selective asymmetric Michael reactions of aldehydes and nitroolefins catalyzed by a primary amine/thiourea.

Authors: Hisatoshi Uehara; Carlos F Barbas
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. Density functional study of enantioselectivity in the 2-methylproline-catalyzed alpha-alkylation of aldehydes.

Authors: Aiping Fu; Benjamin List; Walter Thiel
Journal: J Org Chem Date: 2006-01-06 Impact factor: 4.354

9. Catalytic asymmetric intramolecular alpha-alkylation of aldehydes.

Authors: Nicola Vignola; Benjamin List
Journal: J Am Chem Soc Date: 2004-01-21 Impact factor: 15.419

10. Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts.

Authors: Svetlana B Tsogoeva; Shengwei Wei
Journal: Chem Commun (Camb) Date: 2006-02-23 Impact factor: 6.222

21 in total

Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

1. Titanium(IV)-catalyzed dynamic kinetic asymmetric transformation of alcohols, silyl ethers, and acetals under carbon allylation.

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

3. Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

4. Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Review 5. (Thio)urea organocatalysis--what can be learnt from anion recognition?

6. Light in aminocatalysis: the asymmetric intermolecular alpha-alkylation of aldehydes.

7. anti-Selective asymmetric Michael reactions of aldehydes and nitroolefins catalyzed by a primary amine/thiourea.

8. Density functional study of enantioselectivity in the 2-methylproline-catalyzed alpha-alkylation of aldehydes.

9. Catalytic asymmetric intramolecular alpha-alkylation of aldehydes.

10. Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts.

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

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

3. Mechanism-Guided Development of a Highly Active Bis-thiourea Catalyst for Anion-Abstraction Catalysis.

4. Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

5. Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

6. Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

7. Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

8. Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

9. Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors.

10. Anion-Abstraction Catalysis: The Cooperative Mechanism of α-Chloroether Activation by Dual Hydrogen-Bond Donors.