Traceless Rhodium‐Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β‐Aryl Ketones

Bouisseau, Anaïs; Gao, Ming; Willis, Michael C.

doi:10.1002/chem.201604035

Cited by 11 publications

(5 citation statements)

References 65 publications

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“…The product was prepared according to GP-I from the corresponding α,β-unsaturated alcohol (300.0 mg) to afford 1y (190.0 mg) as a colorless liquid in 64% yield (step 3). Spectroscopic data are in good agreement with reported values …”

Section: Experimental Sectionsupporting

confidence: 90%

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

2019

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A simple yet highly effective approach toward enantioselective synthesis of trans-3,4-disubstituted glutarimides from readily available starting materials is developed using oxidative N-heterocyclic carbene catalysis. The catalytic reaction involves a formal [3 + 3] annulation between enals and substituted malonamides enabling the production of glutarimide derivatives in a single chemical operation via concomitant formation of C−C and C−N bonds. The reaction offers easy access to a broad range of functionalized glutarimides with excellent enantioselectivity and good yield. Synthetic application of the method is demonstrated via formal synthesis of (−)-paroxetine and other bioactive molecules.

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Section: Experimental Sectionsupporting

confidence: 90%

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

2019

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“…Retrosynthetic disconnection of (+)‐yashabushitriol following our approach would provide a highly convergent assembly from oxime 1a , enal 2b easily prepared in one step and keto‐acid 3a (Scheme ).…”

Section: Figurementioning

confidence: 99%

Three‐Component Multi‐Catalytic Enantioselective Oxa‐Michael/Aldolization Sequence and Application to (+)‐Yashabushitriol Synthesis

2020

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By a selective three-component multi-catalytic sequence, amino-catalyzed oxa-Michael addition of oximes to α,-unsaturated aldehydes has been combined with a coppercatalyzed decarboxylative aldolization. This one-pot procedure enables the rapid construction of functionalized ketodiol scaffolds in 85 to 94% ee. Simple reduction of both the resulting Polyketides are ubiquitous in natural products and drugs with unique properties resulting from their ability to form selective hydrogen-bonding frameworks (Figure 1). [1] Therefore, the discovery of efficient and selective methods for the preparation of such complex organic scaffolds has exalted scientific curiosity for decades. [2] However, despite the considerable progress observed in catalytic enantioselective synthesis notably through [a

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“…For example, imines generated from 3-methyl-2-aminopyridine with aldehydes allowed regioselective transition metal-catalyzed hydroacylation assisted by chelation (Scheme 1b). [29][30][31][32][33][34][35] In addition, β-S-substituted aldehydes, [36][37][38][39][40][41][42] salicylaldehydes, [43][44][45][46][47] and N-sulfonyl 2-aminobenzaldehydes, 48 which bear chelating groups, have also been used successfully for transition metalcatalyzed intermolecular hydroacylations (Scheme 1b). These elegant strategies based on chelating groups promoted the formation of linear ketones and avoided the decarbonylation reaction.…”

Section: Introductionmentioning

confidence: 99%

Base-Promoted Catalyst-Free Regioselective Hydroacylation of Styrenes with Hydrazones via Carbanion Addition

et al. 2022

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We report a base-promoted catalyst-free protocol for the highly regioselective hydroacylation of styrenes with hydrazones derived from naturally abundant aldehydes. This protocol generated linear ketones with good functional group tolerance and a broad substrate scope under mild conditions. Mechanistic studies showed that the addition of hydrazone anion to a styrene double bond was the key step, different from previous hydroacylation pathways (via organometallic complexes or radical intermediates). Density functional theory calculations illustrated that the interaction between the potassium cation of hydrazone salt with the arene ring of styrene was critical in facilitating the reaction and controlling regioselectivity.

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Traceless Rhodium‐Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β‐Aryl Ketones

Cited by 11 publications

References 65 publications

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

Three‐Component Multi‐Catalytic Enantioselective Oxa‐Michael/Aldolization Sequence and Application to (+)‐Yashabushitriol Synthesis

Base-Promoted Catalyst-Free Regioselective Hydroacylation of Styrenes with Hydrazones via Carbanion Addition

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