Regional convergence in the reaction of heterosubstituted allylic carbanions via allylic aluminum and boron ate complexes

Yamamoto, Yoshinori; Yatagai, Hidetaka; Saito, Yoshinobu

doi:10.1021/jo00180a027

Cited by 74 publications

(20 citation statements)

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“…The resulting carbanion, however, exhibits ambident properties and furnishes mixtures of isomeric products in reactions with electrophiles. 213 To ensure the required regiodirectivity, the reagent is treated with Lewis acids; the ate-complex thus formed reacts with an aldehyde to give the `normal' product 201.…”

Section: The Krief Reaction and Other Olefination Methodsmentioning

confidence: 99%

Synthetic methodologies for carbo-substituted conjugated dienes

Васильев¹,

Serebryakov²

2001

Russ. Chem. Rev.

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We report the observation of changes in the wave turbulence properties of gravitycapillary surface waves due to a finite-depth effect. When the fluid depth is decreased, a hump is observed on the wave spectrum in the capillary regime at a scale that depends on the depth. The possible origin of this hump is discussed. In the gravity regime, the wave spectrum still shows a power law but with an exponent that strongly depends on the depth. A change in the scaling of the gravity spectrum with the mean injected power is also reported. Finally, the probability density function of the wave amplitude rescaled by its rms value is found to be independent of the fluid depth and to be well described by a Tayfun distribution.

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Section: The Krief Reaction and Other Olefination Methodsmentioning

confidence: 99%

Synthetic methodologies for carbo-substituted conjugated dienes

Васильев¹,

Serebryakov²

2001

Russ. Chem. Rev.

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“…6,7 The 1phenyselenoallyllithium (2) formed reacts principally at the αposition with alkyl halides and epoxides, 6 and at the γ-position with aldehydes and ketones. 6, 8 If (2) is treated with Triethylaluminum prior to reaction with carbonyl compounds, mainly αhydroxyalkylation is observed. 8 Representative regioselectivities are shown in eq 2.…”

Section: Metalationmentioning

confidence: 99%

“…6, 8 If (2) is treated with Triethylaluminum prior to reaction with carbonyl compounds, mainly αhydroxyalkylation is observed. 8 Representative regioselectivities are shown in eq 2. Altered reactivity and well-defined regioselectivity can also be achieved by prior conversion to phenylselenoallylstannanes (3), which react at the α-position with cationic electrophiles such as iminium salts (eq 3).…”

Section: Metalationmentioning

confidence: 99%

“…14 The reaction of (1) with Triethylborane forms the alkylated allylboronate (6) by B to C alkyl transfer with displacement of the PhSe group. This boronate complex can be trapped with aldehydes, or allowed to rearrange to (7) before trapping, to give regioisomeric homoallyl alcohols (8) and (9), in ratios of 94:6, and 9:91, respectively (eq 7). 15 There are also reports of allyl radical transfer from (1) to carbon 16 …”

Section: Se Phmentioning

confidence: 99%

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Allyl Phenyl Selenide

Reich

2001

Encyclopedia of Reagents for Organic Synthesis

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“…In the latter, more common case, the protected alcohol is either already implemented in the allyl species or another transient functional group is used, which can be subsequently cleaved to give the free alcohol (Figure B). This has been extensively studied using various metals, such as B, ,, Sn, , Zn, , In, Al, or Ti . An excellent overview of the available methods and their respective applications in total synthesis was published by Lombardo and Trombini. , Although this strategy is very established, also in an enantioselective fashion, − it displays some major drawbacks.…”

mentioning

confidence: 99%

Direct Access to Monoprotected Homoallylic 1,2-Diols via Dual Chromium/Photoredox Catalysis

et al. 2020

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Herein, we present a dual catalytic strategy to efficiently obtain mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. The modularity of our approach is shown by the introduction of several silyl-and alkyl-based protecting groups, enabling a diverse protecting group strategy. To highlight functional group tolerance and chemoselectivity, we demonstrate the functionalization of a variety of aliphatic, aromatic and heteroaromatic aldehydes, even in presence of ketones and esters. The applicability was further supported by a large scale experiment and a robustness screening. Mechanistic studies support a radical mechanism, starting from the single electron oxidation of the silyl enol ether, facilitated by the β-silicon effect.

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Regional convergence in the reaction of heterosubstituted allylic carbanions via allylic aluminum and boron ate complexes

Cited by 74 publications

References 0 publications

Synthetic methodologies for carbo-substituted conjugated dienes

Synthetic methodologies for carbo-substituted conjugated dienes

Allyl Phenyl Selenide

Direct Access to Monoprotected Homoallylic 1,2-Diols via Dual Chromium/Photoredox Catalysis

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