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Literature DB >> 28164699

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

Jessica A Griswold¹, Matthew A Horwitz¹, Leslie V Leiva¹, Jeffrey S Johnson¹.

Abstract

A quinidine-catalyzed diastereoselective addition of α-angelica lactone to β-halo-α-ketoesters is reported. The α-angelica lactone displays unusual regioselectivity in this reaction, acting as a nucleophile at the α-position to provide fully substituted glycolic esters with three contiguous stereocenters. Subsequent diastereoselective hydrogenation provides an additional stereocenter within the lactone.

Entities: Chemical Gene

Mesh：

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Year: 2017 PMID： 28164699 PMCID： PMC5324730 DOI： 10.1021/acs.joc.6b03059

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

22 in total

1. Resurrecting the Cornforth model for carbonyl addition: studies on the origin of 1,2-asymmetric induction in enolate additions to heteroatom-substituted aldehydes.

Authors: David A Evans; Sarah J Siska; Victor J Cee
Journal: Angew Chem Int Ed Engl Date: 2003-04-17 Impact factor: 15.336

2. Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins.

Authors: Madhu Sudan Manna; Vikas Kumar; Santanu Mukherjee
Journal: Chem Commun (Camb) Date: 2012-04-18 Impact factor: 6.222

3. 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

4. Catalytic asymmetric formal γ-allylation of deconjugated butenolides.

Authors: Amit K Simlandy; Santanu Mukherjee
Journal: Org Biomol Chem Date: 2016-06-15 Impact factor: 3.876

5. 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

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

1. Resurrecting the Cornforth model for carbonyl addition: studies on the origin of 1,2-asymmetric induction in enolate additions to heteroatom-substituted aldehydes.

2. Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins.

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

4. Catalytic asymmetric formal γ-allylation of deconjugated butenolides.

5. 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.

6. Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone.

7. Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions.

8. Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters.

9. Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.

10. Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.

1. Palladium-Catalyzed β-Arylation of α-Keto Esters.

2. 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene.