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Literature DB >> 15149215

A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones.

Ryo Shintani¹, Norihito Tokunaga, Hidenori Doi, Tamio Hayashi.

Abstract

A rhodium-catalyzed asymmetric 1,4-addition reaction has been applied to the synthesis of 2-aryl-4-piperidones. While other conventional nucleophiles fail, organozinc reagents have been successfully utilized for the construction of these useful compounds in very good yield and enantiomeric excess.

Entities: Chemical

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Year: 2004 PMID： 15149215 DOI： 10.1021/ja048825m

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

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Cited

8 in total

1. Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors: Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal: J Org Chem Date: 2010-10-15 Impact factor: 4.354

2. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors: Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal: J Org Chem Date: 2006-10-27 Impact factor: 4.354

A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones.

1. Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

2. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

3. Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

4. Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP.

5. Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

6. Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone.

7. Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors.

8. Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions.