Organocatalytic enantioselective α-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals

Zhang, Huanrui; Wang, Baomin; Cui, Longchen; Li, Ying; Qü, Jingping; Song, Yuming

doi:10.1039/c4ob01921k

Cited by 28 publications

(12 citation statements)

References 50 publications

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“…Then, Wang et al. developed a quinine mediated enantioselective α‐amination of 5‐substituted rhodanines for the construction of chiral N , S ‐acetal motifs . With 2‐aryl‐5‐methylthiazol‐4‐ones as sulfur‐bound pronucleophiles, Palomo et al.…”

Section: Methodsmentioning

confidence: 99%

Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals

et al. 2020

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A chiral phosphoric acid catalyzed stereoselective Michael addition of 5H‐thiazol‐4‐ones to arylazocarboxylates was developed for the construction of optically active N,S‐acetal frameworks. Both 1‐naphthylazocarboxylates and phenylazocarboxylates were compatible to afford a series of 1,4‐adducts in generally high yields and enantioselectivities. Notably, the catalytic protocol enables the formation of N,S‐acetals featuring thiazol‐4‐one skeleton.

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Section: Methodsmentioning

confidence: 99%

Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals

et al. 2020

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“…In 2014, Wang et al. developed a chiral tertiary amine catalyzed α‐amination of 5‐substituted rhodanines to furnish chiral N , S ‐acetals in high yields and enantioselectivities (Scheme D) . The investigation of the azodicarboxylate partner indicated that the ester moiety has a profound effect on the asymmetric induction.…”

Section: Methodsmentioning

confidence: 99%

Organocatalytic Asymmetric Michael Addition of Rhodanines to Azadienes for Assembling of Sulfur‐containing Tetrasubstituted Carbon Stereocenters

Lin

Zhang

et al. 2018

Adv Synth Catal

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“…The organocatalytic enantioselective α‐amination of 5‐substituted rhodanines are established by Wang et al. to furnish chiral N,S ‐acetals in high yields and enantioselectivities (Scheme F) . The evaluation of the azodicarboxylate partner reveals that the ester moiety has a profound effect on the asymmetric induction.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Construction of Vicinal Sulfur‐containing Tetrasubstituted Stereocenters via Organocatalyzed Mannich‐Type Addition of Rhodanines to Isatin Imines

et al. 2018

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The catalyzed enantioselective nucleophilic addition of rhodanines has been established by employing isatin-derived imines as suitable partners under chiral squaramide catalysis. By using this strategy, the resulting 3-substituted 3-amino-2oxindoles featuring both rhodanine and vicinal sulfur-containing tetrasubstituted stereocenters structural motifs were obtained in high yields with excellent enantioselectivities and diastereoselectivities.Skeletons with sulfur-containing tetrasubstituted carbon stereocenters are prevalent substructures found in natural products, drugs, and biologically active compounds (Scheme 1A). [1] The asymmetric construction of these framework has gained much attention and a variety of catalytic enantioselective reactions have been developed over the last decade. [2] In particular, the enantioselective nucleophilic addition of sulfurcontaining prochiral carbon centers offers a direct and efficient access to sulfur-functionalized quaternary carbon stereocenters. For example, the reaction of 5Hthiazol-4-ones has been successfully applied in the catalytic enantioselective construction of sulfur-containing tetrasubstituted carbon stereocenters (Scheme 1B). [3] Although structurally related to 5H-thiazol-4-ones, rhodanines have scarcely been employed in the asymmetric transformation in spite of the importance of being privileged scaffolds in drug discovery (Scheme 1C). [4] Until recently, the group of Ye has developed a primary amine-mediated 1,4-conjugate addition of substituted rhodanines to a,b-unsaturated ketones (Scheme 1D). [5] However, impressive results are mostly limited to acyclic a,b-unsaturated ketones and substrate dependence of catalytic system still remains an important issue. Several cases on the 1,4conjugate addition of N-phenylrhodanine to a,bunsaturated carbonyl compounds are reported by Veselý et al. and sulfur-containing spirocyclic compounds are obtained in moderate yields with stereoselectivities fluctuating over a great range (Scheme 1E). [6] The organocatalytic enantioselective aamination of 5-substituted rhodanines are established by Wang et al. to furnish chiral N,S-acetals in high yields and enantioselectivities (Scheme 1F). [7] The evaluation of the azodicarboxylate partner reveals that the ester moiety has a profound effect on the asymmetric induction. Despite their elegant works, the catalytic asymmetric nucleophilic additions of rhodanines for the construction of sulfur-containing tetrasubstituted carbon stereocenter are still rather limited. The challenges inherent in such transformations mainly include 1) finding the suitable partner to react with rhodanines; and 2) overcoming difficulties in enantiofacial control due to the lesser steric dissimilarity of non-hydrogen substituents on the prochiral carbons; and 3) solving the strong coordinating and adsorptive properties of sulfur species. [8] Therefore, finding a suitable reaction partner and developing catalytic enantioselective nucleophilic addition of rhodanines for the construction of sulfurcontaining tetr...

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Organocatalytic enantioselective α-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals

Cited by 28 publications

References 50 publications

Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals

Organocatalytic Enantioselective α‐Amination by Conjugate Addition of 5H‐Thiazol‐4‐ones to Arylazocarboxylates: Access to Chiral N,S‐acetals

Organocatalytic Asymmetric Michael Addition of Rhodanines to Azadienes for Assembling of Sulfur‐containing Tetrasubstituted Carbon Stereocenters

Enantioselective Construction of Vicinal Sulfur‐containing Tetrasubstituted Stereocenters via Organocatalyzed Mannich‐Type Addition of Rhodanines to Isatin Imines

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