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Literature DB >> 15984850

Organocatalytic asymmetric direct alkylation of alpha-diazoester via C-H bond cleavage.

Daisuke Uraguchi¹, Keiichi Sorimachi, Masahiro Terada.

Abstract

A new variant of phosphoric acid-catalyzed C-C bond forming reaction, direct alkylation of alpha-diazoester, via C-H bond cleavage is presented. The resulting products, beta-amino-alpha-diazoesters, are highly functionalized and useful synthetic precursors for various types of beta-amino acids.

Entities: Chemical

Year: 2005 PMID： 15984850 DOI： 10.1021/ja051922a

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

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Cited

12 in total

Review 1. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors: Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal: Chem Rev Date: 2011-06-28 Impact factor: 60.622

2. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors: Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2014-07-01 Impact factor: 15.336

3. Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

Authors: Guilong Li; Matthew J Kaplan; Lukasz Wojtas; Jon C Antilla
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

4. Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Authors: Yi Luan; Yue Qi; Hongyi Gao; Qianqian Ma; Scott E Schaus
Journal: European J Org Chem Date: 2014-11-01

5. Generation and exploitation of acyclic azomethine imines in chiral Brønsted acid catalysis.

Authors: Takuya Hashimoto; Hidenori Kimura; Yu Kawamata; Keiji Maruoka
Journal: Nat Chem Date: 2011-07-22 Impact factor: 24.427

6. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

Authors: Anton V Gulevich; Victoria Helan; Donald J Wink; Vladimir Gevorgyan
Journal: Org Lett Date: 2013-02-01 Impact factor: 6.005

Organocatalytic asymmetric direct alkylation of alpha-diazoester via C-H bond cleavage.

Review 1. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

2. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

3. Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

4. Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

5. Generation and exploitation of acyclic azomethine imines in chiral Brønsted acid catalysis.

6. Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

7. Isotope effects and mechanism of the asymmetric BOROX Brønsted acid catalyzed aziridination reaction.

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

9. PREPARATION OF ISOPROPYL 2-DIAZOACETYL(PHENYL)CARBAMATE.

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