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Literature DB >> 20481613

Catalytic nucleophilic glyoxylation of aldehydes.

Abstract

Beta-silyloxy-alpha-keto esters are prepared through a cyanide-catalyzed benzoin-type reaction with silyl glyoxylates and aldehydes. The products undergo a dynamic kinetic resolution to provide enantioenriched orthogonally protected alcohols and can be converted to the corresponding beta-silyloxy-alpha-amino esters.

Entities: Chemical Gene Species

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Year: 2010 PMID： 20481613 PMCID： PMC2890213 DOI： 10.1021/ol100996w

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

23 in total

1. Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate.

Authors: Wengang Yao; Jianbo Wang
Journal: Org Lett Date: 2003-05-01 Impact factor: 6.005

Review 2. Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts.

Authors: Takao Ikariya; A John Blacker
Journal: Acc Chem Res Date: 2007-10-26 Impact factor: 22.384

3. Catalytic asymmetric acylation of (silyloxy)nitrile anions.

Authors: David A Nicewicz; Christopher M Yates; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2004-05-10 Impact factor: 15.336

4. Diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes catalyzed by a chiral Ni(OAc)(2) complex under mild conditions.

Authors: Ayako Nakamura; Sylvain Lectard; Daisuke Hashizume; Yoshitaka Hamashima; Mikiko Sodeoka
Journal: J Am Chem Soc Date: 2010-03-31 Impact factor: 15.419

5. Asymmetric hydrogenation of aromatic ketones catalyzed by the TolBINAP/DMAPEN-ruthenium(II) complex: a significant effect of N-substituents of chiral 1,2-diamine ligands on enantioselectivity.

Authors: Hirohito Ooka; Noriyoshi Arai; Keita Azuma; Nobuhito Kurono; Takeshi Ohkuma
Journal: J Org Chem Date: 2008-10-17 Impact factor: 4.354

6. Metallophosphites as umpolung catalysts: the enantioselective cross silyl benzoin reaction.

Authors: Xin Linghu; Justin R Potnick; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2004-03-17 Impact factor: 15.419

7. Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors: Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal: J Am Chem Soc Date: 2008-10-04 Impact factor: 15.419

8. Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates.

Authors: Stephen N Greszler; Jeffrey S Johnson
Journal: Org Lett Date: 2009-02-19 Impact factor: 6.005

9. Kinetic control in direct alpha-silyloxy ketone synthesis: a new regiospecific catalyzed cross silyl benzoin reaction.

Authors: Xin Linghu; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2003-06-06 Impact factor: 15.336

10. Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

Authors: Barry M Trost; Sushant Malhotra; Benjamin A Fried
Journal: J Am Chem Soc Date: 2009-02-11 Impact factor: 15.419

9 in total

1. Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

Authors: Kimberly M Steward; Emily C Gentry; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2012-04-17 Impact factor: 15.419

2. Asymmetric synthesis of α-keto esters via Cu(II)-catalyzed aerobic deacylation of acetoacetate alkylation products: an unusually simple synthetic equivalent to the glyoxylate anion synthon.

Authors: Kimberly M Steward; Jeffrey S Johnson
Journal: Org Lett Date: 2011-04-12 Impact factor: 6.005

Catalytic nucleophilic glyoxylation of aldehydes.

1. Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate.

Review 2. Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts.

3. Catalytic asymmetric acylation of (silyloxy)nitrile anions.

4. Diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes catalyzed by a chiral Ni(OAc)(2) complex under mild conditions.

5. Asymmetric hydrogenation of aromatic ketones catalyzed by the TolBINAP/DMAPEN-ruthenium(II) complex: a significant effect of N-substituents of chiral 1,2-diamine ligands on enantioselectivity.

6. Metallophosphites as umpolung catalysts: the enantioselective cross silyl benzoin reaction.

7. Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

8. Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates.

9. Kinetic control in direct alpha-silyloxy ketone synthesis: a new regiospecific catalyzed cross silyl benzoin reaction.

10. Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

1. Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

2. Asymmetric synthesis of α-keto esters via Cu(II)-catalyzed aerobic deacylation of acetoacetate alkylation products: an unusually simple synthetic equivalent to the glyoxylate anion synthon.

3. Three-component glycolate Michael reactions of enolates, silyl glyoxylates, and α,β-enones.

4. Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.

5. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

6. Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

7. Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters.

8. Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters.

9. Alternaric acid: formal synthesis and related studies.