A new approach to the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans by the 1,5-CH insertion reaction of magnesium carbenoids

Satoh, Tsuyoshi; Yasoshima, Tsukasa; Momochi, Hitoshi

doi:10.1016/j.tetlet.2012.02.034

Cited by 5 publications

(3 citation statements)

References 36 publications

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“…This elegant approach allows for the introduction of aromatic groups at position 6 of the spirocyclic system (Scheme 106). 127 As highlighted throughout the preceding discussion, advances in Au-and Ag-catalyzed reactions provide novel entries and opportunities for the synthesis of spirocycles. Accordingly, silver-catalyzed cycloaddition of the allyl ether and propargyl alcohol in 430 provides functionalized spirocyclic allenes such as 431.…”

Section: -Oxaspiromentioning

confidence: 99%

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Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities

2014

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Section: -Oxaspiromentioning

confidence: 99%

“…This reactive species then undergoes [1,5]-CH insertion with the benzyl ether to give 429 . This elegant approach allows for the introduction of aromatic groups at position 6 of the spirocyclic system (Scheme ) …”

Section: Synthetic Strategies Toward the Synthesis Of Spiro[3n]alkanesmentioning

confidence: 99%

Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities

2014

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“…The reaction of 3-alkoxy-substituted 1-chloroalkyl ptolyl sulfoxides 118 possessing no C-H bond at the 3-position with i-PrMgCl afforded tetrahydrofurans 120 (Scheme 31). 48 Magnesium carbenoids 119 selectively inserted into the intramolecular methylene C-H bond adjacent to the oxygen atom. In this case, 1,5-C-H insertion occurred preferentially over a 1,2-hydride shift.…”

Section: 5-c-h Insertions Of Magnesium Carbenoidsmentioning

confidence: 99%

Recent Advances in Magnesium Carbenoid Chemistry

Kimura

2017

Synthesis

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Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.1 Introduction2 Structures of Magnesium Carbenoids3 Reactions of Magnesium Carbenoids as Nucleophiles3.1 Nucleophilic Reactions of Magnesium Carbenoids3.2 Nucleophilic Reactions of Magnesium Alkylidene Carbenoids3.3 Nucleophilic Reactions of Cyclopropylmagnesium Carbenoids4 Electrophilic Reactions of Magnesium Carbenoids4.1 Reactions with Nucleophiles Followed by Electrophiles4.2 Reactions with Nucleophiles Possessing Electrophilic Functional Groups4.3 Nucleophilic Substitution Followed by β-Elimination5 Rearrangements of Magnesium Carbenoids5.1 1,2-Shifts of Magnesium Carbenoids5.2 1,3-C–H Insertions of Magnesium Carbenoids5.3 1,5-C–H Insertions of Magnesium Carbenoids5.4 [2+1] Cycloaddition of a Magnesium Carbenoid6 Conclusion and Outlook

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ChemInform Abstract: A New Approach to the Synthesis of 1‐Oxaspiro[4.n]alkanes and Tetrahydrofurans by the 1,5‐CH Insertion Reaction of Magnesium Carbenoids.

2012

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A New Approach to the Synthesis of 1-Oxaspiro[4.n]alkanes and Tetrahydrofurans by the 1,5-CH Insertion Reaction of Magnesium Carbenoids. -Treatment of substrates (I), (III) and (V) with iPrMgCl leads to formation of the carbenoid intermediates which undergo 1,5-CH insertion reaction to give the target skeletons, in part substructures of natural substances. Sulfoxide (VII) lacking an ether functional group provides the desired spirodecane (VIII) only as minor product. -(SATOH*, T.; YASOSHIMA, T.; MOMOCHI, H.; Tetrahedron Lett. 53 (2012) 16, 2074-2077, http://dx.

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A new approach to the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans by the 1,5-CH insertion reaction of magnesium carbenoids

Cited by 5 publications

References 36 publications

Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities

Four-Membered Ring-Containing Spirocycles: Synthetic Strategies and Opportunities

Recent Advances in Magnesium Carbenoid Chemistry

ChemInform Abstract: A New Approach to the Synthesis of 1‐Oxaspiro[4.n]alkanes and Tetrahydrofurans by the 1,5‐CH Insertion Reaction of Magnesium Carbenoids.

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