Preparation and Use of Enantioenriched Allenylsilanes for the Stereoselective Synthesis of Homopropargylic Ethers

Brawn, Ryan A.; Panek, James S.

doi:10.1021/ol070936d

Cited by 65 publications

(39 citation statements)

References 20 publications

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“…31,32 It is worth mentioning that the key formation of the allenylsilanes was performed in refluxing xylenes with a catalytic amount of propionic acid on a 25 mmol scale. (R)-24 afforded (S a )-25 in 79% yield and 98% ee while (S)-24 afforded (R a )-25 in 81% yield and 98% ee.…”

Section: Propargyl Vinyl Ethers As Reactive Intermediatesmentioning

confidence: 99%

Propargyl Claisen rearrangement: allene synthesis and beyond

et al. 2013

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The propargyl Claisen rearrangement is a known protocol to gain access to functionalized allenes through the [3,3]-sigmatropic transformation of propargyl vinyl ethers. The correct use of appropriate propargyl vinyl ethers as starting materials coupled with suitable reaction conditions can aid in the development of new domino methodologies in which the allenes are valuable intermediates in route to a wide range of important classes of organic compounds.

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Section: Propargyl Vinyl Ethers As Reactive Intermediatesmentioning

confidence: 99%

Propargyl Claisen rearrangement: allene synthesis and beyond

et al. 2013

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“…[197] Allenes can serve as carbon nucleophiles in the synthesis of homopropargylic ethers. [198] The chiral propargylic alcohols (S)-380 382 in 81 % yield and 98 % ee. [198] The chiral propargylic alcohols (S)-380 382 in 81 % yield and 98 % ee.…”

Section: Other Applications -Syntheses Of Building Blocks Intermediamentioning

confidence: 99%

“…To this end, a straightforward method for the preparation of highly enantioenriched allenylsilanes through Johnson-Claisen rearrangement was developed by Panek and co-workers. [198] The chiral propargylic alcohols (S)-380 382 in 81 % yield and 98 % ee. Similarly, (R)-380 gave (S a )-382 in 79 % yield and 98 % ee.…”

Section: Other Applications -Syntheses Of Building Blocks Intermediamentioning

confidence: 99%

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

2013

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The orthoester Johnson–Claisen rearrangement, an important C–C bond forming reaction, has been used enormously in the past four decades in the synthesis of bioactive molecules, natural products, synthetic intermediates, analogues, and useful building blocks. The method has also featured in chemical modification of materials. This review covers developments in this rearrangement since 2003. Unlike many other forms of Claisen rearrangement, this reaction is generally a one‐pot, one‐step process. It is compatible with numerous functional groups, despite its use of acid catalysis, and offers chirality transfer to produce stereoselective products. The method also offers opportunities for rapid modifications to various functionalized compounds and building blocks for further synthetic exploration.

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“…These approaches are now accepted as viable ecologically benign alternatives. Aryl substituted ethers are commercially pretty because of their wide range of applications in biology such as analgesic [16,17] , anti-inflammatory [16] and antipyretic drugs [18] , environmentally clean flavors to motor oils, high-octane gasoline additives and their non-toxic properties [19,20] . As continuation of our work is to improve the alkoxylation under microwave irradiation, ultrasound irradiation [10,21,22] , we had reacted the benzyl alcohol with p-bromotoluene using phase transfer catalysis and explored the various studies.…”

Section: Introductionmentioning

confidence: 99%