The first example of regiospecific magnesium carbenoid 1,3-CH insertion: its mechanism and stereochemistry

Ogata, Shingo; Masaoka, Shigeyuki; Sakai, Ken; Satoh, Tsuyoshi

doi:10.1016/j.tetlet.2007.05.101

Cited by 24 publications

(10 citation statements)

References 33 publications

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“…A similar cyclopropane formation through magnesium carbenoid C-H insertion has been reported by Satoh and coworkers, but the system was set up such that no b hydrogens were present [51,52].…”

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Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

Davies

Dick

2009

C-H Activation

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The functionalization of carbon-hydrogen bonds through transition metal carbenoid insertion is becoming a powerful method for the construction of new carbon-carbon bonds in organic synthesis. This chapter will highlight recent developments in this field, while placing it within its historical context. Intramolecular carbenoid C-H insertion will be covered first, focusing on formation of three-and six-membered rings, as well as the use of nontraditional substrates. Additionally, the most recent progress in asymmetric catalysis will be discussed. The bulk of the chapter will concentrate on intermolecular transformations, emphasizing both the effect of substrate structure and the influence of carbene substituent electronics on the regioselectivity of the reactions. Vinyldiazoacetates will be covered as a distinct class of carbenoid precursors, as they have been shown to initiate a variety of unique transformations, such as the combined C-H activation/Cope rearrangement. Finally, the synthetic utility of carbenoid C-H insertion reactions, both intra-and intermolecular, will be displayed through their use in the total syntheses of a number of natural products and pharmaceuticals.

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confidence: 58%

“…These include copper [36][37][38][39][40][41][42][43][44][45], silver [46,47], iron [48][49][50], gold [40], and magnesium [51,52], and most will be discussed in context, particularly in Sect. 3.1.…”

Section: Fig 3 Chiral Dirhodium Catalysts Discussed In This Chaptermentioning

confidence: 99%

Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

Davies

Dick

2009

C-H Activation

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“…16 Based on the results mentioned above, adduct 4a was determined to be (2R,3R,4S,S R )-4-chloro-2-methyl-3-phenyl-4-(p-tolylsulfinyl)butylic acid tert-butyl ester, as shown in Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

Sugiyama

Nakaya

Satoh

2008

Tetrahedron: Asymmetry

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“…7 The absolute configuration of the carbon bearing a 2-phenylethyl group 7 and the carbon bearing a chlorine atom 8 of 6 was determined to be (R) and (S), respectively, based on our previous studies (Scheme 2). 7,8 Adduct 6 was treated with i-PrMgCl (ether solution) in toluene at À78°C and the temperature of the reaction mixture was slowly …”

Section: Resultsmentioning

confidence: 99%

Asymmetric synthesis of bicyclo[n.1.0]alkanes by the enantioselective 1,3-CH insertion reaction of chiral magnesium carbenoids

Satoh

Kuramoto

Ogata

et al. 2010

Tetrahedron: Asymmetry

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The first example of regiospecific magnesium carbenoid 1,3-CH insertion: its mechanism and stereochemistry

Cited by 24 publications

References 33 publications

Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

Asymmetric synthesis of bicyclo[n.1.0]alkanes by the enantioselective 1,3-CH insertion reaction of chiral magnesium carbenoids

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