Magnesium-induced regiospecific C-silylation of suitably substituted enoates and dienoates

Kundu, Pintu K.; Ghosh, Sunil K.

doi:10.1016/j.tet.2010.09.001

Cited by 8 publications

(2 citation statements)

References 76 publications

(16 reference statements)

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“…Conversely, the addition of 4 equiv of TMSCl greatly improved the reaction efficiency, leading to a 70% yield of 2a (entry 8). The use of a further increased amount of TMSCl led to the formation of the β-silylated compound as the byproduct . The investigation on the amount of methyl acrylate was also performed at the same time, and the results indicated that 4 equiv of methyl acrylate were appropriate (entries 9 and 10).…”

Section: Resultsmentioning

confidence: 99%

Regioselective Coupling of Different Conjugate Esters by Magnesium Metal Reduction: A Route to Unsymmetrical Adipic Acid Esters

Zhang,

Mori

et al. 2023

J. Org. Chem.

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A novel tactic to synthesize unsymmetrical 3-aryladipic acid esters has been developed via magnesium-promoted reductive coupling of ethyl cinnamates with methyl acrylate. In the present methodology, 3-aryladipic acid derivatives were prepared with good functional group tolerance and a wide substrate scope under very mild reaction conditions in good yields. The application of this reaction to dienic acid esters led to the successful control of the reaction to give 5-aryl-oct-3-enedioic acid esters with high regioselectivity.

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Section: Resultsmentioning

confidence: 99%

Regioselective Coupling of Different Conjugate Esters by Magnesium Metal Reduction: A Route to Unsymmetrical Adipic Acid Esters

Zhang,

Mori

et al. 2023

J. Org. Chem.

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“…49 Later, a sterically more demanding disilylmethyl group was introduced at the fourth position, whilst the substituent at the fifth position was removed to afford the 1,2,4-trisubstituted [3]dendralene 29b. A Mg-mediated reductive silylation 50 of β-dimethyl(phenyl)silyl acrylate using TMSCl afforded the disilyl propionate 30b, which was transformed into the desired [3]dendralene 29b (Scheme 13) following the aforementioned protocol (see Scheme 12). 49 Hence, we could successfully synthesize stable and highly functionalized [3]dendralenes bearing silylmethyl functionality.…”

Section: Account Syn Lettmentioning

confidence: 99%

[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds

Ghosh

Naidu

Singh

2017

Synlett

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[3]Dendralenes are exquisite molecules as they exhibit enormous potential for the rapid generation of architecturally esoteric scaffolds when subjected to tandem Diels–Alder reactions, but their synthesis is a tall order. In conjunction with diversity-oriented synthesis, [3]dendralenes satisfy the potential demand for simultaneous and efficient synthesis of intricate collections of molecules that exhibit a range of activities for lead generation in drug discovery. This account chronicles our roller-coaster journey and systematic approach beginning from the synthesis of extremely unstable, non-isolable [3]dendralenes through moderately stable examples and then finally, highly functionalized, stable [3]dendralenes via sequential methylenation (using dimethylsulfonium methylide) and Horner–Wadsworth–Emmons olefination. It also describes the study of the attributes affecting their stability and reactivity with various dienophiles. In addition, it reports on how these dendralenes, upon astute maneuvering, can be engaged in a diene-transmissive Diels–Alder (DTDA) sequence, thus harnessing their full potential by construction of a small but diverse library of complex frameworks in a quick and efficient manner, with step and atom economy.1 Introduction2 Literature Methods for [3]Dendralene Synthesis3 Our Tryst with [3]Dendralenes3.1 Serendipitous Olefination with the Corey–Chaykovsky Ylide3.2 Synthesis of [3]Dendralenes and Reactivity/Stability Studies3.3 Diels–Alder Reactions of [3]Dendralenes3.4 Tuning of [3]Dendralenes for the DTDA Reactions3.5 Diversity-Oriented Synthesis with [3]Dendralenes3.6 Rationalization of Factors Governing the Stability and Reactivity of [3]Dendralenes4 Conclusions

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Allylchlorodimethylsilane*

Nevill

2015

Encyclopedia of Reagents for Organic Synthesis

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Magnesium-induced regiospecific C-silylation of suitably substituted enoates and dienoates

Cited by 8 publications

References 76 publications

Regioselective Coupling of Different Conjugate Esters by Magnesium Metal Reduction: A Route to Unsymmetrical Adipic Acid Esters

Regioselective Coupling of Different Conjugate Esters by Magnesium Metal Reduction: A Route to Unsymmetrical Adipic Acid Esters

[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds

Allylchlorodimethylsilane*

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