Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes

Kimura, Midori; Matsuda, Yukiko; Koizumi, Akihiro; Tokumitsu, Chihiro; Tokoro, Yuichiro; Fukuzawa, Shin Ichi

doi:10.1016/j.tet.2015.08.002

Cited by 23 publications

(8 citation statements)

References 25 publications

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“…In 2016, Fukuzawa et al employed an alternative chiral silver complex derived from AgOAc and ferrocenyl chiral ligand 5 to promote asymmetric domino reactions between imino esters 2/7 and nitroalkenes 6. 7 As illustrated in Scheme 2, chiral pyrrolidines 8 were obtained in good yields (47-86%), diastereoselectivities (76-92% de) and enantioselectivities (86-97% ee) from sequential Michael and aza-Henry reactions.…”

Section: Five-membered Ringsmentioning

confidence: 99%

The Use of Domino Reactions for the Synthesis of Chiral Rings

Pellissier

2020

Synthesis

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This short review highlights the recent developments reported in the last four years on the asymmetric construction of chiral rings based on enantioselective domino reactions promoted by chiral metal catalysts.1 Introduction2 Formation of One Ring Containing One Nitrogen Atom3 Formation of One Ring Containing One Oxygen/Sulfur Atom4 Formation of One Ring Containing Several Heterocyclic Atoms5 Formation of One Carbon Ring6 Formation of Two Rings7 Conclusion

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Section: Five-membered Ringsmentioning

confidence: 99%

The Use of Domino Reactions for the Synthesis of Chiral Rings

Pellissier

2020

Synthesis

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“…112). A plausible mechanism proposed by the authors suggests that the formation of indenoquinoxaline-11-one 43, from condensation reac-tion of 1,2-phenylenediamine (110) and ninhydrin 57, and subsequent reaction with sarcosine (13) and decarboxylation affords the corresponding azomethine ylide. Then, stereoselective 1,3-DC with the dipolarophile 114 (derived from the aldehyde 112 and 111) produces the desired dispiroindenequinoxalinepyrrolidines 113 (Scheme 33).…”

Section: Short Review Syn Thesismentioning

confidence: 99%

“…AgOAc•ThioClickFerrophos (TCF) 254 complex, acting in a bifunctional mode, was the best catalyst to yield the corresponding endo-cycloadducts 255 (Scheme 73). 110,111…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

2017

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In this revision a summary of the trends of the formation of complex or not so complex heterocyclic structures through 1,3-DC of azomethine ylides is described. Diastereo-and enantioselective processes as well as nonasymmetric cycloadditions constitute very important synthetic tools for achieving all these series of compounds. The contents are classified as follows: 1. Introduction 2. Synthesis of spiroxindoles 3. Synthesis of spiropyrrolidines 4. Synthesis of spiropiperidines and piperidines 5. Synthesis of pyrrolidines and fused pyrrolidines 6. Synthesis of pyrrolizidines and indolizidines 7. Synthesis of quinolone and isoquinolines 8. Conclusions

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“…In addition, an endo -selective version of these processes was described by Fukuzawa et al, in 2016 . It involved the use of 5 mol % of AgOAc combined with the same quantity of ThioClickFerrophos ligand 63 in 1,4-dioxane at room temperature.…”

Section: Silver-catalyzed 13-dipolar Cycloadditionsmentioning

confidence: 99%

“…In addition, an endo-selective version of these processes was described by Fukuzawa et al, in 2016. 190 corresponding chiral pyrrolidines 113 as endo-cycloadducts in moderate to good yields of 51−86%, good to high diastereoselectivities (82−92% de), and enantioselectivities of 86−97% ee (Scheme 43). In the case of the reaction of an alkyl imino ester (R = Cy), both lower yield and diastereoselectivity were obtained (47% yield and 76% de) albeit with high enantioselectivity (93% ee).…”

Section: Formal 13-dipolar Cycloadditions Of Glycine Imino Esters And...mentioning

confidence: 99%