Phosphine‐Catalyzed [3+2] Cycloaddition of Aza‐Aurones and Allenoates: Enantioselective Synthesis of 2‐Spirocyclopentyl‐Indolin‐3‐Ones

Brambilla, Elisa; Pozza, Camilla; Rizzato, Silvia; Abbiati, Giorgio; Pirovano, Valentina

doi:10.1002/ejoc.202201385

Cited by 5 publications

(2 citation statements)

References 51 publications

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“…Recently, Pirovano and co-workers reported that the reaction of azaaurones 211 with allenoates was efficiently promoted by endo-Ph-HypPhos to give spirocyclic products 212 with complete regioselectivity and high levels of enantioselectivity (Scheme 232). 676 Duan, Li, and co-workers used a pair of pseudoenantiomer ligands, (S P ,R,R S )-JiaPhos (L128a) and (R P ,S,R S )-JiaPhos (L128b), in the [4 + 2] annulation reactions between 3methylene-2-oxindoles and γ-benzyl allenoates. 304,677 The respective reactions proceeded in the presence of a catalytic amount of benzoic acid at 50 °C to provide the enantiomers of 3′-spirocyclic oxindoles with high to excellent enantiomeric excesses (Scheme 233).…”

Section: Kinetic Resolution Of Secondary Alcoholsmentioning

confidence: 99%

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Imamoto

2024

Chem. Rev.

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Chiral phosphorus ligands play a crucial role in asymmetric catalysis for the efficient synthesis of useful optically active compounds. They are largely categorized into two classes: backbone chirality ligands and P-stereogenic phosphorus ligands. Most of the reported ligands belong to the former class. Privileged ones such as BINAP and DuPhos are frequently employed in a wide range of catalytic asymmetric transformations. In contrast, the latter class of P-stereogenic phosphorus ligands has remained a small family for many years mainly because of their synthetic difficulty. The late 1990s saw the emergence of novel P-stereogenic phosphorus ligands with their superior enantioinduction ability in Rh-catalyzed asymmetric hydrogenation reactions. Since then, numerous P-stereogenic phosphorus ligands have been synthesized and used in catalytic asymmetric reactions. This Review summarizes P-stereogenic phosphorus ligands reported thus far, including their stereochemical and electronic properties that afford high to excellent enantioselectivities. Examples of reactions that use this class of ligands are described together with their applications in the construction of key intermediates for the synthesis of optically active natural products and therapeutic agents. The literature covered dates back to 1968 up until December 2023, centering on studies published in the late 1990s and later years.

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Section: Kinetic Resolution Of Secondary Alcoholsmentioning

confidence: 99%

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Imamoto

2024

Chem. Rev.

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“…Cyclization product 3g is obtained via acid-promoted nucleophilic addition of indole C2 carbon to the distal carbonyl of indole-1,2-dione 3f, followed by re-aromatization. 125 …”

Section: Gold Catalyzed Quinoline Reactionsmentioning

confidence: 99%

Advances in gold catalyzed synthesis of quinoid heteroaryls

Majeed,

Zafar,

Mushtaq

et al. 2024

RSC Adv.

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Phosphine‐Catalyzed 1,6‐Addition and Tandem Addition/Self‐Aldol Condensation Reactions of Para‐Quinone Methides with Thiols

Zhong,

Li,

Zhang

et al. 2024

Eur J Org Chem

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Phosphine‐catalyzed chemodivergent reactions of para‐quinone methides (p‐QMs) affording a wide variety of diarylmethyl thioether derivatives have been reported. In the transformation presented in this work, P(4‐FC6H4)3 catalyzed the direct 1,6‐addition of p‐QMs with thiols, whereas P(4‐MeC6H4)3 promoted the tandem addition/self‐aldol condensation reactions of p‐QMs with 1,4‐dithiane‐2,5‐diol. Moreover, some of the obtained products were screened against cancer cell lines HepG2, NB4, and K562, and one was found to inhibit the proliferation of all the tested cancer cell types

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Phosphine‐Catalyzed [3+2] Cycloaddition of Aza‐Aurones and Allenoates: Enantioselective Synthesis of 2‐Spirocyclopentyl‐Indolin‐3‐Ones

Abstract: An enantioselective phosphine-catalyzed [3 + 2] cycloaddition between aza-aurones and allenoates is here described. The reaction proceeded under mild reaction conditions to afford 2-spirocyclopentyl indolin-3-one derivatives as single γ-isomer and with high levels of stereocontrol.

Cited by 5 publications

References 51 publications

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Advances in gold catalyzed synthesis of quinoid heteroaryls

Phosphine‐Catalyzed 1,6‐Addition and Tandem Addition/Self‐Aldol Condensation Reactions of Para‐Quinone Methides with Thiols

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