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Literature DB >> 12197731

A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimethylsilyl)diazomethane in a regiospecific and highly stereoselective manner.

Varinder K Aggarwal¹, Chris G Sheldon, Gregor J Macdonald, William P Martin.

Abstract

The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates.

Entities: Chemical

Year: 2002 PMID： 12197731 DOI： 10.1021/ja027061c

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

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Cited

8 in total

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Journal: Org Lett Date: 2015-12-01 Impact factor: 6.005

3. Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors: Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal: J Am Chem Soc Date: 2013-12-17 Impact factor: 15.419

4. Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors: Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal: J Am Chem Soc Date: 2013-01-17 Impact factor: 15.419

A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimethylsilyl)diazomethane in a regiospecific and highly stereoselective manner.

1. Catalytic ester-amide exchange using group (IV) metal alkoxide-activator complexes.

2. Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

3. Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

4. Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

5. Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

6. Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers.

7. Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation.

8. Sodium Diisopropylamide-Mediated Dehydrohalogenations: Influence of Primary- and Secondary-Shell Solvation.