Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

• Hao Guo,
• Yu-Fei Ao,
• De-Xian Wang and
• Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

• established the optimal reaction conditions, the substrate scope was explored. Reactions of various isatin imines 6a–w with MAHT 7a were firstly investigated (Scheme 2). Different N-substituents on isatins caused a significant effect. For non-substituted (6b) or other substrates with larger substituents (6c–g

• M1, M5, M7, and M8 was previously reported [30]. Substrate scope of isatin imines. Reaction conditions: 6 (0.2 mmol), 7a (0.3 mmol), and 5 mol % M3 in 2 mL of CPME (cyclopentyl methyl ether). Substrate scope of MAHTs. Reaction conditions: 6a (0.2 mmol), 7 (0.3 mmol), and 5 mol % M3 in 2 mL of CPME

Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines

• Marco Manenti,
• Leonardo Lo Presti,
• Giorgio Molteni and
• Alessandra Silvani

Beilstein J. Org. Chem. 2022, 18, 303–308, doi:10.3762/bjoc.18.34

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• recently, the strategy via introducing secondary interactions for the design of the bifunctional catalysts achieved wide application in asymmetric reactions [74]. Wu et al. described a Mannich asymmetric addition of cyanocoumarins 39 to isatin imines 112 catalyzed by an amide-phosphonium salt 114. This

• of 2-hydroxycinnamaldehydes 109 with 4-hydroxycoumarins 1. Mannich asymmetric addition of cyanocoumarins 39 to isatin imines 112 catalyzed by the amide-phosphonium salt 114. Enantioselective total synthesis of (+)-scuteflorin A (119). Funding The authors gratefully acknowledge FAPESP (grants 2013

Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines

• Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 1349–1369, doi:10.3762/bjoc.14.114

• imines published since the beginning of 2015. Keywords: asymmetric synthesis; chiral 3-amino-2-oxindoles; chirality; isatin imines; nucleophilic addition; Introduction Chiral oxindoles represent an important class of products widely present in nature and exhibiting many biological activities. Among

• organocatalyzed methodologies [10][13]. The simplest method to prepare chiral quaternary 3-amino-2-oxindoles is based on enantioselective catalytic nucleophilic additions to isatin imines. This is not only because of the easy access to isatin imines, but also by the possibility of using a wide range of

• additions to isatin imines have been developed, including Mannich reactions, aza-Morita–Baylis–Hillman reactions, Friedel–Crafts reactions, aza-Henry reactions, additions of heteronucleophiles, Strecker reactions, among others. The goal of this review is to update the catalytic asymmetric synthesis of

Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts

• Hee Seung Jang,
• Yubin Kim and
• Dae Young Kim

Beilstein J. Org. Chem. 2016, 12, 1551–1556, doi:10.3762/bjoc.12.149

• reaction time, and low temperature required for good enantioselectivity. Thus, new approaches for the organocatalytic enantioselective addition of diphenyl phosphonate to isatin imines are highly desired. In connection with our ongoing research program on the design and application in asymmetric catalysis

• ). The reaction of diphenyl phosphonate (2) with N-allylated and 5-halo-N-allylated isatin imines provided adducts 3a–d in good yields (80–94%) with excellent enantioselectivities (93–97% ee, Table 2, entry 1–4). The addition of diphenyl phosphonate (2) to 5-chloro-N-substituted isatin imines 1e and 1f

Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations

• Ouldouz Ghashghaei,
• Consiglia Annamaria Manna,
• Esther Vicente-García,
• Marc Revés and
• Rodolfo Lavilla

Beilstein J. Org. Chem. 2014, 10, 12–17, doi:10.3762/bjoc.10.3

• nitrilium intermediate, in agreement with a Sorensen report (Scheme 4, route iii) [21]. Finally, the imino-nitrilium cation can be trapped by an aromatic ring when using isatin imines, leading to bis(imino)tetrahydroquinoline 8, (Scheme 4, route iv). In a reaction using a large isocyanide excess, a triple