Cationic Palladium Complex‐Catalyzed Diastereoselective Tandem Annulation of 2‐Iminoarylboronic Acids with Substituted Alkynes: Enantioselective Synthesis of Aminoindene Derivatives by Double Asymmetric Induction

Yu, Xufen; Lu, Xin

doi:10.1002/adsc.201100363

Cited by 21 publications

(7 citation statements)

References 68 publications

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“…Moreover, the same authors have recently reported the synthesis of chiral aminoindene derivatives 15a – h on the basis of a diastereo‐ and enantioselective domino annulation reaction of ( S )‐2‐( N ‐ tert ‐butanesulfinylimino)arylboronic acids 13a – d as chiral auxiliaries with a variety of alkynes 14a – e 24. The reaction was catalyzed by chiral cationic palladium complex, {Pd[( S,S )‐bdpp](H 2 O) 2 } 2+ (BF 4 − ) 2 , affording through double asymmetric induction the corresponding sulfoxides 15a – h as mixtures of two diastereomers.…”

Section: One‐ and Two‐component Domino Reactionsmentioning

confidence: 99%

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Ahn

Kim

Lee

et al. 2010

Phytotherapy Research

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Chronic kidney disease (CKD) is a common cause of end-stage renal disease. Antihypertensive agents are used clinically to inhibit the progression of CKD, but cannot prevent eventual renal failure. This study investigated the effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, in rats suffering from CKD induced by 5/6 nephrectomy. After development of renal insufficiency, the rats were treated with Tanshinone IIA (10 mg/kg) for 8 weeks. Serum creatinine, angiotensin II (Ang II), transforming growth factor β1 (TGF-β1) and collagen IV levels were significantly reduced in Tanshinone IIA treated rats compared with a control group. In addition, Tanshinone IIA suppressed increases in urinary protein excretion in CKD rats. These findings suggest that chronic oral administration of Tanshinone IIA can improve renal dysfunction associated with CKD.

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Section: One‐ and Two‐component Domino Reactionsmentioning

confidence: 99%

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Ahn

Kim

Lee

et al. 2010

Phytotherapy Research

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“…Because of this, only very few methods concerning the asymmetric cyclization for the synthesis of chiral 1aminoindenes have been reported. [42] And only two studies including ours do not involve the formation of a quaternary chiral carbon. In 2018, we have reported the first Co-catalyzed enantioselective cyclization to synthesize the chiral 1-aminoindenes (Scheme 30).…”

Section: Co-catalyzed Intramolecular 12-insertion Of Iminementioning

confidence: 82%

Transition‐Metal‐Catalyzed Addition/Cyclization Reactions of the C−N Multiple Bonds Containing Species

Hsieh

2021

The Chemical Record

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This article describes our research work for the past decade, which involves the transition-metal-catalyzed cyclization reactions of the CÀ N multiple bonds containing species and their synthetic applications to access various heterocyclic compounds. The concepts of reactions including four types of coupling with a subsequent cyclization are (1) the transitionmetal performs as a Lewis acid to activate a nitrile and accelerate the nucleophilic addition, (2) the transition-metal-catalyzed 1,2-insertion reaction of nitrile, (3) the Cu-catalyzed CÀ N coupling reaction of imine, and (4) the Co-catalyzed addition/cyclization reaction of imine. These methods can be used to synthesize various N-containing aromatic heterocycles with higher efficiency, and can be applied to the synthesis of relevent natural alkaloids, their derivatives as well as biologically active compounds.

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“…2‐Formylphenylboronic acid ( 2 d ), which exists in a tautomeric equilibrium with oxaborole in solution, [46] produces the product in 21% yield. To our delight, the imine 2 e [47] could be used as an alternative substrate to the aldehyde substrate 2 d to produce 3 ae in 53% yield. 2‐Acetylphenylboronic acid ( 2 f ) in the absence of the above‐mentioned equilibrium afforded 3 af in 68% yield.…”

Section: Resultsmentioning

confidence: 99%

Nickel(II)‐Mediated C−S Cross‐Coupling Between Thiols and ortho‐Substituted Arylboronic Acid

et al. 2021

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Herein, we report a C−S cross‐coupling reaction between alkyl thiols or aryl thiols and ortho‐substituted arylboronic acids that proceeds in the presence of an inexpensive and ligand‐free NiCl2 ⋅ 6H2O salt and N‐methylmorpholine, a weak base, at 25 °C in air. The presence of coordinating and electron‐withdrawing groups at the ortho‐position of the arylboronic acids played a crucial role in determining the efficiency of the reaction. X‐ray crystallographic analysis revealed that the [NiCl2(DMF)2(H2O)2] complex was formed in‐situ. The complex is an excellent precursor of the active nickel species. The reaction offers an extremely mild and operationally convenient method to access a wide variety of alkyl aryl sulfides and diaryl sulfides without using expensive transition metals, such as palladium, gold, and rhodium, and specialized and expensive ligands.

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Cationic Palladium Complex‐Catalyzed Diastereoselective Tandem Annulation of 2‐Iminoarylboronic Acids with Substituted Alkynes: Enantioselective Synthesis of Aminoindene Derivatives by Double Asymmetric Induction

Cited by 21 publications

References 68 publications

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Transition‐Metal‐Catalyzed Addition/Cyclization Reactions of the C−N Multiple Bonds Containing Species

Nickel(II)‐Mediated C−S Cross‐Coupling Between Thiols and ortho‐Substituted Arylboronic Acid

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