One pot iridium-catalyzed asymmetrical double allylations of sodium sulfide: a fast and economic way to construct chiral C2-symmetric bis(1-substituted-allyl)sulfane

Shi, Zheng; Huang, Wei‐Qing; Gao, Ning; Cui, Ruimin; Zhang, Min; Zhao, Xiaoming

doi:10.1039/c1cc11930c

Cited by 43 publications

(15 citation statements)

References 72 publications

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“…On the other hand, Zhao et al. have recently developed an enantioselective pseudo‐three‐component reaction based on double allylations of sodium sulfide 182. The reaction was catalyzed by a chiral iridium complex, in situ generated from [Ir(cod)Cl] 2 and chiral phosphoramidite ligand 284 , in the presence of cesium fluoride and water, yielding the corresponding enantiopure chiral C 2 ‐symmetric bis(1‐substituted‐allyl)sulfanes 285a – h in good to excellent yields and diastereoselectivities of up to >98% de , as shown in Scheme .…”

Section: Multicomponent 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: Multicomponent 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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“…The Zhao group reported a series of asymmetric double allylations of sodium sulfide to provide bis(1-substituted allyl)sulfanes (Scheme 22). 48 The inclusion of water through the use of sodium sulfide nonahydrate was found to be essential to achieving high yields. In a representative example, sulfone 88 was synthesized through the addition of mchloroperoxybenzoic acid in one pot after the iridium catalysis reaction.…”

Section: Scheme 21 Ring-closing Metathesis To Afford 3-sulfolenesmentioning

confidence: 99%

“…Treatment of 88 with Grubbs I catalyst afforded the trans-2,5-dimethyl-3-sulfolene as a single enantiomeric form. 48 The Hayashi group reported a method to access chiral 3arylsulfolanes 90 in high enantiomeric excess using a chiral rhodium catalyst. 49 The reaction was shown to proceed in high yield and high enantioselectivity with 2-sulfolene or 3-sulfolene under the optimized conditions.…”

Section: Scheme 21 Ring-closing Metathesis To Afford 3-sulfolenesmentioning

confidence: 99%

3-Sulfolenes and Their Derivatives: Synthesis and Applications

Brant

Wulff

2015

Synthesis

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The diverse substitution patterns available to 3-sulfolenes have long made them useful for the preparation of multi-substituted 1,3-diene equivalents. More recently, the 3-sulfolene motif itself (or its reduced sulfolane congener) is finding increasing application as a structural element in the creation of molecules for biological applications. This review describes various methods to afford 3-sulfolene building blocks and their derivatives. Selected applications in synthetic and medicinal chemistry are also discussed. 1 Introduction 2 The Preparation of Monocyclic Sulfolene Building Blocks 2.1 Sulfolenes through Electrophilic Addition 2.1.1 Sulfolenes through Nucleophilic Addition to 4-Bromo-2-sulfolene 2.2 Sulfolenes through Oxidation of a Thiol Precursor 2.3 Sulfolenes through Noble Metal Catalysis 2.4 Sulfolenes through Deprotonation Followed by Alkylation 3 Synthesis of Bicyclic Sulfolenes and Their Derivatives 3.

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“…In addition, (R)-281a-n could be further converted through a single step into corresponding (Z)--branched derivatives with retention of configuration. [182] The reaction was catalyzed by a chiral iridium complex, in situ generated from [Ir(cod)Cl] 2 and chiral phosphoramidite ligand 284, in the presence of cesium fluoride and water, yielding the corresponding enantiopure chiral C 2 -symmetric bis(1-substituted-allyl)sulfanes 285a-h in good to excellent yields and diastereoselectivities of up to > 98% de, as shown in Scheme 78. This work constituted the first example in which sodium sulfide was employed as an atom-economical inorganic nucleophile in transition-metal-catalyzed allylation substitutions.…”

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confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

2012

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International audienceSince the first definition of domino reactions by Tietze in 1993, an explosive number of these fascinating reactions have been developed, allowing easily building complex chiral molecular architectures from simple materials to be achieved in a single step. Even more interesting, the possibility to join two or more reactions in one asymmetric domino process catalyzed by chiral metal catalysts has rapidly become one challenging goal for chemists, due to economical advantages, such as avoiding costly protecting groups and time-consuming purification procedures after each step. The explosive development of enantioselective metal-catalyzed domino including multicomponent reactions is a consequence of the considerable impact of the advent of asymmetric transition-metal catalysis. This review aims to update the last developments of enantioselective one-, two-and multicomponent domino reactions mediated by chiral metal catalysts, covering the literature since the beginning of 2006

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One pot iridium-catalyzed asymmetrical double allylations of sodium sulfide: a fast and economic way to construct chiral C2-symmetric bis(1-substituted-allyl)sulfane

Cited by 43 publications

References 72 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

3-Sulfolenes and Their Derivatives: Synthesis and Applications

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

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