Deoxygenation of .alpha.,.beta.-unsaturated aldehydes and ketones via the catecholborane reduction of the corresponding tosylhydrazones

Kabalka, George W.; Yang, Dayu; Baker, John D.

doi:10.1021/jo00865a043

Cited by 93 publications

(33 citation statements)

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“…We envisaged that a stereoselective [3,3]-sigmatropic rearrangement of intermediate 20 might afford a cis -fused decalin derivative with an olefin in the desired position. 15 To this end, aldehyde 17 was converted to enone 19 through allylic oxidation of amide 18 . 16 Treatment of this enone with tosylhydrazine followed by diastereoselective reduction 15c of the corresponding hydrazone gave us intermediate 20 (R = Weinreb amide), which underwent stereoselective rearrangement to form cis -decalin 21 .…”

Section: Resultsmentioning

confidence: 99%

“…15 To this end, aldehyde 17 was converted to enone 19 through allylic oxidation of amide 18 . 16 Treatment of this enone with tosylhydrazine followed by diastereoselective reduction 15c of the corresponding hydrazone gave us intermediate 20 (R = Weinreb amide), which underwent stereoselective rearrangement to form cis -decalin 21 . 15a,15b Ketone 22 was then obtained after the addition of furanyl Grignard reagent to amide 21 .…”

Section: Resultsmentioning

confidence: 99%

“…16 Treatment of this enone with tosylhydrazine followed by diastereoselective reduction 15c of the corresponding hydrazone gave us intermediate 20 (R = Weinreb amide), which underwent stereoselective rearrangement to form cis -decalin 21 . 15a,15b Ketone 22 was then obtained after the addition of furanyl Grignard reagent to amide 21 . In the absence of MgBr 2 salt, the furanyl lithium reagent also reacted with the angular ester group.…”

Section: Resultsmentioning

confidence: 99%

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Stereoselective Total Synthesis of Hainanolidol and Harringtonolide via Oxidopyrylium-Based [5 + 2] Cycloaddition

2013

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The tetracyclic carbon skeleton of hainanolidol and harringtonolide was efficiently constructed by an intramolecular oxidopyrylium-based [5+2] cycloaddition. An anionic ring opening strategy was developed for the cleavage of the ether bridge in 8-oxabicyclo[3.2.1]octenes derived from the [5+2] cycloaddition. Conversion of cycloheptadiene to tropone was realized by a sequential [4+2] cycloaddition, Kornblum-DeLaMare rearrangement, and double elimination. The biomimetic synthesis of harringtonolide from hainanolidol was also confirmed.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Stereoselective Total Synthesis of Hainanolidol and Harringtonolide via Oxidopyrylium-Based [5 + 2] Cycloaddition

2013

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“…Such reduction can be performed with mild borane reducing agents such as catecholboranes. Tosylhydrazide intermediates have been identified and studied [117,118]. Other reducing agents compatible with this transformation are lithium aluminum hydride [119] and the milder sodium cyanoborohydride [120].…”

Section: Caglioti Reaction: Reduction Of Tosylhydrazones [115]mentioning

confidence: 99%

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Luca

Fenwick

2015

Journal of Photochemistry and Photobiology B: Biology

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Available online xxxx a b s t r a c tThe present review covers organic transformations involved in the reduction of CO 2 to chemical fuels. In particular, we focus on reactions of CO 2 with organic molecules to yield carboxylic acid derivatives as a first step in CO 2 reduction reaction sequences. These biomimetic initial steps create opportunities for tandem electrochemical/chemical reductions. We draw parallels between long-standing knowledge of CO 2 reactivity from organic chemistry, organocatalysis, surface science and electrocatalysis. We point out some possible non-faradaic chemical reactions that may contribute to product distributions in the production of solar fuels from CO 2 . These reactions may be accelerated by thermal effects such as resistive heating and illumination.

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“…The conditions we employed previously largely followed Kabalka’s protocol. 20 After reduction of the hydrazone with catecholborane was complete, solid NaOAc hydrate was added and the mixture heated under reflux.…”

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confidence: 99%

Synthesis of the C21–C34 fragment of antascomicin B

Hutchison

Gibson

McIntosh

2011

Tetrahedron Letters

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Deoxygenation of .alpha.,.beta.-unsaturated aldehydes and ketones via the catecholborane reduction of the corresponding tosylhydrazones

Cited by 93 publications

References 0 publications

Stereoselective Total Synthesis of Hainanolidol and Harringtonolide via Oxidopyrylium-Based [5 + 2] Cycloaddition

Stereoselective Total Synthesis of Hainanolidol and Harringtonolide via Oxidopyrylium-Based [5 + 2] Cycloaddition

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Synthesis of the C21–C34 fragment of antascomicin B

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