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Asymmetric organocatalytic synthesis of chiral homoallylic amines
- Nikolay S. Kondratyev and
- Andrei V. Malkov
Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201
- , encompassing cutting-edge advances in hydrogen-bond catalysis and non-classical approaches. Furthermore, practical examples showcasing the application of these innovative methodologies in total synthesis are presented. Keywords: asymmetric catalysis; asymmetric synthesis; chiral amines; organicatalysis
Graphical Abstract
Scheme 1: The position of homoallylic amines in the landscape of alkaloid and nitrogen compounds syntheses.
Scheme 2: 3,3’-Diaryl-BINOL-catalysed asymmetric organocatalytic allylation of acylimines [24].
Scheme 3: Aminophenol-catalysed reaction between N-phosphinoylimines and pinacol allylboronic ester. Imine sc...
Scheme 4: Asymmetric geranylation and prenylation of indoles catalysed by (R)- or (S)-3,3’-dibromo-BINOL [25]. aA...
Scheme 5: (R)-3,3’-Di(3,5-di(trifluoromethyl)phenyl-BINOL-catalysed asymmetric geranylation and prenylation o...
Scheme 6: Microwave-induced one-pot asymmetric allylation of in situ-formed arylimines, catalysed by (R)-3,3’...
Scheme 7: Microwave-induced one-pot asymmetric allylation of in situ-formed arylimines, catalysed by (R)-3,3’...
Scheme 8: Kinetic resolution of chiral secondary allylboronates [15,30].
Scheme 9: (E)-Stereospecific asymmetric α-trifluoromethylallylation of cyclic imines and hydrazones [31].
Scheme 10: Hosomi–Sakurai-type allylation of in situ-formed N-Fmoc aldimines [32].
Figure 1: Two different pathways for the Hosomi–Sakurai reaction of allyltrimethylsilane with N-Fmoc aldimine...
Scheme 11: Chiral squaramide-catalysed hydrogen bond-assisted chloride abstraction–allylation of N-carbamoyl α...
Figure 2: The pyrrolidine unit gem-methyl group conformational control in the squaramide-based catalyst [34].
Figure 3: The energetic difference between the transition states of the two proposed modes of the reaction (SN...
Scheme 12: One-pot preparation procedure for oxazaborolidinium ion (COBI) 63 [37].
Scheme 13: Chiral oxazaborolidinium ion (COBI)-catalysed allylation of N-(2-hydroxy)phenylimines with allyltri...
Scheme 14: The two-step N-(2-hydroxy)phenyl group deprotection procedure [37].
Scheme 15: Low-temperature (−40 °C) NMR experiments evidencing the reversible formation of the active COBI–imi...
Figure 4: Two computed reaction pathways for the COBI-catalysed Strecker reaction (TS1 identical to allylatio...
Scheme 16: Highly chemoselective and stereospecific synthesis of γ- and γ,δ-substituted homoallylic amines by ...
Scheme 17: Catalytic cycle for the three-component allylation with HBD/πAr–Ar catalyst [39].
Scheme 18: Reactivity of model electrophiles [39].
Scheme 19: HBD/πAr–Ar catalyst rational design and optimisation [39].
Scheme 20: Scope of the three-component HBD/πAr–Ar-catalysed reaction [39].
Scheme 21: Limitations of the HBD/πAr–Ar-catalysed reaction [39].
Scheme 22: Asymmetric chloride-directed dearomative allylation of in situ-generated N-acylquinolinium ions, ca...
Scheme 23: Chiral phosphoric acid-catalysed aza-Cope rearrangement of in situ-formed N-α,α’-diphenyl-(α’’-ally...
Scheme 24: Tandem (R)-VANOL-triborate-catalysed asymmetric aza-Cope rearrangement of in situ-formed aldimines ...
Scheme 25: (S)-TRIP-catalysed enantioconvergent aza-Cope rearrangement of β-formyl amides, substrate scope [43]. a...
Scheme 26: (S)-TRIP-catalysed enantioconvergent aza-Cope rearrangement of β-formyl amides 16–19, amide and all...
Scheme 27: Synthetic applications of homoallylic N-benzophenone imine products 131 [43].
Scheme 28: Chiral organocatalysed addition of 2,2,2-trifluoroethyl ketimines to isatin-derived Morita–Baylis–H...
Scheme 29: Chiral chinchona-derived amine-catalysed reaction between isatin-based Morita–Baylis–Hilman carbona...
Scheme 30: (R)-VAPOL-catalysed hydrogen atom transfer deracemisation [45].
Scheme 31: Chiral PA-catalysed [1,3]-rearrangement of ene-aldimines [46].
