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Literature DB >> 15606110

Dichloromethane activation. Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF.

Tu-Hsin Yan¹, Chia-Chung Tsai, Ching-Ting Chien, Chia-Ching Cho, Pei-Chen Huang.

Abstract

[reaction: see text] This Mg-TiCl4-promoted CH2-transfer reaction of CH2Cl2 represents an extremely simple, practical, and efficient methylenation of a variety of ketones and aldehydes, especially in enolizable or sterically hindered ketones such as 2,2-dimethylcyclohexanone, camphor, and fenchone.

Entities: Chemical

Year: 2004 PMID： 15606110 DOI： 10.1021/ol0478887

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

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Cited

7 in total

1. Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR.

Authors: James R Woods; Mark V Riofski; Mary M Zheng; Melissa A O'Banion; Huaping Mo; Julia Kirshner; David A Colby
Journal: Bioorg Med Chem Lett Date: 2013-09-06 Impact factor: 2.823

Review 2. Catalytic Enantioselective Dihalogenation in Total Synthesis.

Authors: Matthew L Landry; Noah Z Burns
Journal: Acc Chem Res Date: 2018-04-17 Impact factor: 22.384

3. Synthesis of cycloheptanoid natural products via tandem 5-exo cyclization/Claisen rearrangement process.

Authors: Timo V Ovaska
Journal: ARKIVOC Date: 2010-10-31 Impact factor: 1.140

4. Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0]decane skeleton.

Authors: Matthias Breuning; Tobias Häuser; Christian Mehler; Christian Däschlein; Carsten Strohmann; Andreas Oechsner; Holger Braunschweig
Journal: Beilstein J Org Chem Date: 2009-12-21 Impact factor: 2.883

Dichloromethane activation. Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF.

1. Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR.

Review 2. Catalytic Enantioselective Dihalogenation in Total Synthesis.

3. Synthesis of cycloheptanoid natural products via tandem 5-exo cyclization/Claisen rearrangement process.

4. Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0]decane skeleton.

5. A Unified Approach for the Enantioselective Synthesis of the Brominated Chamigrene Sesquiterpenes.

6. Synthesis of racemic β-chamigrene, a spiro[5.5]undecane sesquiterpene [corrected].

Review 7. Total syntheses of strained polycyclic terpenes.