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Literature DB >> 16984158

The [1,5]-Brook rearrangement: an initial application in anion relay chemistry.

Amos B Smith¹, Ming Xian, Won-Suk Kim, Dae-Shik Kim.

Abstract

The [1,5]-Brook rearrangement proceeds efficiently in a series of hydroxyl dithiane substrates with sodium and potassium bases; less effective are lithium bases. That the mode of silyl migration is intramolecular was demonstrated by a crossover experiment. Finally, the tricomponent anion relay chemistry (ARC) coupling tactic was demonstrated employing the [1,5]-Brook rearrangement.

Entities: Chemical

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Year: 2006 PMID： 16984158 DOI： 10.1021/ja065033e

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

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Cited

18 in total

1. Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

Authors: Amos B Smith; Rongbiao Tong; Won-Suk Kim; William A Maio
Journal: Angew Chem Int Ed Engl Date: 2011-08-10 Impact factor: 15.336

2. Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

Authors: Yifan Deng; Minh D Nguyen; Yike Zou; K N Houk; Amos B Smith
Journal: Org Lett Date: 2019-02-26 Impact factor: 6.005

3. Ortho-TMS benzaldehyde: an effective linchpin for type II anion relay chemistry (ARC).

Authors: Amos B Smith; Won-Suk Kim; William M Wuest
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

Authors: Qi Liu; Yu Chen; Xiao Zhang; K N Houk; Yong Liang; Amos B Smith
Journal: J Am Chem Soc Date: 2017-06-14 Impact factor: 15.419

5. Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity.

Authors: Amos B Smith; Won-Suk Kim
Journal: Proc Natl Acad Sci U S A Date: 2011-01-18 Impact factor: 11.205

The [1,5]-Brook rearrangement: an initial application in anion relay chemistry.

1. Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

2. Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

3. Ortho-TMS benzaldehyde: an effective linchpin for type II anion relay chemistry (ARC).

4. Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

5. Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity.

Review 6. Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

7. Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: lessons learned.

8. Benzyl and phenylthiomethyl silanes: a new class of bifunctional linchpins for type II anion relay chemistry (ARC).

9. (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.

10. Long-range anion relay chemistry (LR-ARC): a validated ARC tactic.