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Literature DB >> 16805524

Reductive olefination of aldehydes via chromium Brook rearrangement.

Rachid Baati¹, Charles Mioskowski, Deb Barma, Rajashaker Kache, J R Falck.

Abstract

[reaction: see text] The combination of CrCl(2) and silyl chlorides converts aryl and conjugated aldehydes into olefinic adducts in good to excellent yields. When constrained by structural features, the intermediate vic-diol can be isolated. Available data are consistent with a novel chromium Brook rearrangement.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16805524 PMCID： PMC2517130 DOI： 10.1021/ol0607140

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

3 in total

1. Stanna-Brook rearrangement of carboxylic acid derivatives. Synthetic utility and mechanistic studies.

Authors: M Rita Paleo; M Isabel Calaza; Paula Graña; F Javier Sardina
Journal: Org Lett Date: 2004-03-18 Impact factor: 6.005

2. Asymmetric retro-[1,4] Brook rearrangement and its stereochemical course at silicon.

Authors: Atsuo Nakazaki; Takeshi Nakai; Katsuhiko Tomooka
Journal: Angew Chem Int Ed Engl Date: 2006-03-27 Impact factor: 15.336

3. Effective and highly stereoselective coupling with vinyldiazomethanes to form symmetrical trienes.

Authors: Michael P Doyle; Ming Yan
Journal: J Org Chem Date: 2002-01-25 Impact factor: 4.354

3 in total

4 in total

1. Generation of Nucleophilic Chromium Acetylides from gem-Trichloroalkanes and Chromium Chloride: Synthesis of Propargyl Alcohols.

Authors: Dhurke Kashinath; Steve Tisserand; Narender Puli; John R Falck; Rachid Baati
Journal: European J Org Chem Date: 2010-04-01

Reductive olefination of aldehydes via chromium Brook rearrangement.

1. Stanna-Brook rearrangement of carboxylic acid derivatives. Synthetic utility and mechanistic studies.

2. Asymmetric retro-[1,4] Brook rearrangement and its stereochemical course at silicon.

3. Effective and highly stereoselective coupling with vinyldiazomethanes to form symmetrical trienes.

1. Generation of Nucleophilic Chromium Acetylides from gem-Trichloroalkanes and Chromium Chloride: Synthesis of Propargyl Alcohols.

2. Synthesis and Study of the Antimalarial Cardamom Peroxide.

3. Synthesis of diphenylhexatriene by the Pd-catalyzed dimerization of cinnamyl acetate.

4. Cascade synthesis of (E)-2-alkylidenecyclobutanols.