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Literature DB >> 25671693

Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.

Abstract

Allylic alcohols can be transformed into γ,δ-unsaturated α,α-dibromo esters through a two-step process: formation of a bromal-derived mixed acetal, followed by tandem dehydrobromination/Claisen rearrangement. The scope and selectivity of both steps have been investigated. The product α,α-dibromo esters were subjected to various carbon-carbon bond-forming reactions, oxidations, and lactonizations.

Entities: Chemical Disease Gene

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Year: 2015 PMID： 25671693 PMCID： PMC4482617 DOI： 10.1021/acs.orglett.5b00209

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

18 in total

1. Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes.

Authors: Ryan P Wurz; Gregory C Fu
Journal: J Am Chem Soc Date: 2005-09-07 Impact factor: 15.419

2. Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates.

Authors: Mitsuru Shindo; Yutaka Yoshimura; Maiko Hayashi; Hiroe Soejima; Takashi Yoshikawa; Kenji Matsumoto; Kozo Shishido
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3. Synthesis of tetrasubstituted and functionalized enol ethers by E-selective olefination of esters with ynolates.

Authors: Mitsuru Shindo; Taisuke Kita; Toshihiro Kumagai; Kenji Matsumoto; Kozo Shishido
Journal: J Am Chem Soc Date: 2006-02-01 Impact factor: 15.419

4. Low-temperature n-butyllithium-induced rearrangement of allyl 1,1-dichlorovinyl ethers.

Authors: Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas Minehan
Journal: Org Lett Date: 2006-02-02 Impact factor: 6.005

5. Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes.

Authors: Yang S Tran; Ohyun Kwon
Journal: J Am Chem Soc Date: 2007-10-03 Impact factor: 15.419

6. Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines.

Authors: Hua Xiao; Zhuo Chai; Dongdong Cao; Hongyu Wang; Jinghao Chen; Gang Zhao
Journal: Org Biomol Chem Date: 2012-03-14 Impact factor: 3.876

Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.

1. Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes.

2. Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates.

3. Synthesis of tetrasubstituted and functionalized enol ethers by E-selective olefination of esters with ynolates.

4. Low-temperature n-butyllithium-induced rearrangement of allyl 1,1-dichlorovinyl ethers.

5. Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes.

6. Highly enantioselective [4 + 2] cycloadditions of allenoates and dual activated olefins catalyzed by N-acyl aminophosphines.

7. Synthesis of 2-Deoxy-2-halo-L-ascorbic Acids.

8. PHOSPHINE-CATALYZED [4+2] ANNULATION: SYNTHESIS OF ETHYL 6-PHENYL-1-TOSYL-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATE.

9. A torquoselective 6π electrocyclization approach to reserpine alkaloids.

10. An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

1. Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.