Asymmetric [3+2] annulations of 1,4-di-thiane-2,5-diol and oxindole ketimines

Feng, Boxu; Yang, Jin‐Dong; Li, Jiuyuan; Li, Xin

doi:10.1016/j.tetlet.2016.06.084

Cited by 24 publications

(9 citation statements)

References 67 publications

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“…In this context, Li and co‐workers also reported the same annulation strategy between 1,4‐dithiane‐2,5‐diol and isatin derived ketimine to produce spirocyclic 3‐aminoxindoles with comparable results (Scheme 84). [129] …”

Section: Synthesis Of Five‐ Membered Ringsmentioning

confidence: 99%

Squaramide Catalyzed Asymmetric Synthesis of Five‐ and Six‐Membered Rings

Biswas¹,

Ghosh

Shankhdhar

et al. 2021

Asian J Org Chem

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Chiral analogues of squaramides have been fruitful in organocatalyzed asymmetric reactions over last decade. Alongside other H-bonding catalysts like ureas, thioureas: squaramides have been proved to be efficient asymmetric catalysts for the formation of acyclic and cyclic chiral molecules. A wide range of cyclic molecules bearing multiple functionalities and stereocenters have been synthesized by using several bifunctional squaramides as catalysts. These catalysts perform as base utilizing basic N atom in their chiral extension and help in stereoinduction by forming H-bonds with suitable H-bond acceptors. The present review focuses on assembling recent progresses of asymmetric synthesis of five and six membered rings promoted by squaramides. A handful of articles have been published by several research groups documenting asymmetric construction of five-and six-membered rings as part of interesting and complex molecular architectures. Different methodologies like conventional and formal cycloadditions or cascade reactions have been engineered through the assistance of chiral squaramides to fabricate the carbo-and heterocycles. This review also includes dual and cooperative catalytic system in which squaramide is one of the catalysts.

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Section: Synthesis Of Five‐ Membered Ringsmentioning

confidence: 99%

Squaramide Catalyzed Asymmetric Synthesis of Five‐ and Six‐Membered Rings

Biswas¹,

Ghosh

Shankhdhar

et al. 2021

Asian J Org Chem

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“…The lack of control concerns the hemiaminal stereocenter of derivatives 191 and upon oxidation with PCC the spirothiazolidinones 192 can be obtained in satisfactory overall yield and good enantioselectivity. Very recently a better diastereoselectivity has been recorded for this process ( dr up to 9:1) using the same reactants but a different bifunctional squaramide catalyst . It should be observed that the utilization of ethyl thioglycolate for the same reaction does not provide any thiazolidinone compound of type 192 but the simple linear adduct which can be hardly converted into the spiro derivative …”

Section: Spiroheterocyclic Derivativesmentioning

confidence: 99%

Recent Developments in the Stereoselective Synthesis of Nitrogen‐Containing Heterocycles using N‐Acylimines as Reactive Substrates

Marcantoni

Petrini

2016

Adv Synth Catal

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Scheme 3. Enantioselective synthesis of trans-aziridines 8 catalyzed by chiral phosphoric acid 10. Scheme 4. Enantioselective synthesis of trans-aziridines 14. Scheme5.Preparation of chiral aziridines 17. Scheme6.Synthesis of chiral aziridines 20. Scheme 22. Synthesis of chiral 2-pyrrolines 82. Scheme23. Enantioselective synthesis of epi-cytoxazone 89. Scheme 24. Synthesis of the mGluR5modulator 96. Scheme 25. Synthesis of chiral 1,3-oxazolines. Scheme26. Synthesis of chiral imidazolidin-2-one 102. Scheme 27. Enantioselectiven itro-Mannichr eaction.Scheme28. Synthesis of (À)-nutlin-3 111.Scheme29. Synthesis of functionalized tetrahydropyridines. Scheme 32. Synthesis of chiral piperidines 129. Scheme 33. One-pot synthesis of N-formylpiperidines. Scheme34. Synthesis of bicyclic aminal 136. Scheme 39. General synthesis of isatin ketimines. Scheme 40. Asymmetric Staudinger reaction. Scheme41. Synthesis of spirocyclic oxindolo-g-lactams. Scheme 42. Synthesis of methylidenes pirocyclic compounds. Scheme 43. Synthesis of spirooxindolepyrrolines. Scheme44. Synthesis of imidazoline-based spirooxindoles. Scheme 48. Synthesis of spirolactam derivatives. Scheme49. Synthesis of spirooxindolelactams 201. Scheme50. Synthesis of polycyclic spirolactams 203. Scheme 56. Synthesis of chiral spiroazetidin-2-ones 228.

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“…The same year, Li, Li, and co-workers described an efficient asymmetric [3+2] annulation reaction between isatin imines 5 and 1,4-dithiane-2,5-diol (34) as equal equivalent of 2-mercaptoacetaldehyde (Scheme 9). 15 The domino reaction catalyzed by 35 begins with the addition of 34 to 5, leading to an aldehyde intermediate that subsequently cyclizes into the corresponding chiral product 36. A range of these products were achieved in high yields (75-95%), low to good diastereoselectivities (34-80% de), and good to high enantioselectivities (78-97% ee).…”

Section: Scheme 8 Nhc-catalyzed Domino Michael/lactamization Reactionmentioning

confidence: 99%