Catalytic enantioselective tandem carbonyl ylide formation—intramolecular cycloaddition with unsaturated α-diazo-β,ε-diketo sulfones

Hodgson, David M.; Glen, Rebecca; Redgrave, Alison J.

doi:10.1016/j.tetasy.2009.02.031

Cited by 36 publications

(10 citation statements)

References 16 publications

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“…In addition, Hodgson et al. investigated the enantioselective intramolecular domino carbonyl ylide formation–1,3‐dipolar cycloaddition reaction employing the sulfonyl functionality as a different type of electron‐withdrawing group at the ylidic carbon, specifically using unsaturated α‐diazo‐β,ε‐diketo sulfones 75. Among a series of chiral catalysts tested, chiral dirhodium(II) tetrakis[ N ‐benzene‐fused‐phthaloyl‐( S )‐valinate], Rh 2 ( S ‐BPTV) 4 , provided the best albeit moderate enantioselectivity of 43% ee for the cycloadduct derived from phenyl sulfone along with 75% yield.…”

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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“…The rhodium complex 138 ( Figure 10) (10 mol%) was the best catalyst but the enantioselection of the process was very disappointing (up to 44% ee). 78 High levels of asymmetric induction were observed in the dipole-LUMO/dipolarophile-HOMO controlled cycloaddition reactions between 2-benzopyrilium-4-enolates and vinyl ether derivatives. The difference between Schemes 35 and 36 was that a chiral Lewis acid, apart from the rhodium complex, was required to perform the cycloaddition step in Scheme 36, and consequently no domino sequence existed.…”

Section: Diazoalkanes and Carbonyl Ylidesmentioning

confidence: 98%

Metal complexes versus organocatalysts in asymmetric 1,3-dipolar cycloadditions

Nájera¹,

Sansano²,

Yus³

2010

J. Braz. Chem. Soc.

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Neste review apresentamos uma comparação entre reações de cicloadição 1,3-dipolar catalizadas por ácido de Lewis com as organo catalizadas, com ênfase na síntese enantiosseletiva de sistemas hetero ou carbocíclicos de cinco membros. Essas reações exibem características interessantes, mas a mais importante é a formação de até quatro centro estereogênicos em apenas uma etapa de reação.In this review, a comparison between the Lewis acid catalysed and organocatalysed 1,3-dipolar cycloaddition is presented with special focus on the enantioselective synthesis of five-membered hetero-or carbocyclic systems, is described. These reactions exhibit very interesting features, but the most important one is the generation of up to four stereogenic centres in only one reaction step.

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“…[74] In addition, Hodgson et al investigated the enantioselective intramolecular domino carbonyl ylide formation−1,3-dipolar cycloaddition reaction employing sulfonyl functionality as a different type of electron-withdrawing group at the ylidic carbon, specifically using unsaturated -diazo-,-diketo sulfones. [75] Among a series of chiral catalysts tested, chiral dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-valinate], Rh 2 (S-BPTV) 4 , provided the best albeit moderate enantioselectivity of 43% ee for the cycloadduct derived from phenyl sulfone along with 75% yield. Chiral catalysts of metals other than rhodium, such as nickel and silver, and chiral catalysts of ytterbium have also been employed to induce enantioselective domino carbonyl-ylide formation−1,3dipolar cycloaddition reactions.…”

Section: Domino Carbonyl Ylide Formation-13-dipolar Cycloaddition Rementioning

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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Catalytic enantioselective tandem carbonyl ylide formation—intramolecular cycloaddition with unsaturated α-diazo-β,ε-diketo sulfones

Cited by 36 publications

References 16 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

Metal complexes versus organocatalysts in asymmetric 1,3-dipolar cycloadditions

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

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