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1 article(s) from Fanelli, Rossana

Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts

Laura A. Bryant,
Rossana Fanelli and
Alexander J. A. Cobb

Beilstein J. Org. Chem. 2016, 12, 429–443, doi:10.3762/bjoc.12.46

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Graphical Abstract

Figure 1: The structural diversity of the cinchona alkaloids, along with cupreine, cupreidine, β-isoquinidine...

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Scheme 1: The original 6’-OH cinchona alkaloid organocatalytic MBH process, showing how the free 6’-OH is ess...

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Scheme 2: Use of β-ICPD in an aza-MBH reaction.

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Scheme 3: (a) The isatin motif is a common feature for MBH processes catalyzed by β-ICPD, as demonstrated by ...

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Scheme 4: (a) Chen’s asymmetric MBH reaction. Good selectivity was dependent upon the presence of (R)-BINOL (...

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Scheme 5: Lu and co-workers synthesis of a spiroxindole.

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Scheme 6: Kesavan and co-workers’ synthesis of spiroxindoles.

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Scheme 7: Frontier’s Nazarov cyclization catalyzed by β-ICPD.

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Scheme 8: The first asymmetric nitroaldol process catalyzed by a 6’-OH cinchona alkaloid.

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Scheme 9: A cupreidine derived catalyst induces a dynamic kinetic asymmetric transformation.

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Scheme 10: Cupreine derivative 38 has been used in an organocatalytic asymmetric Friedel–Crafts reaction.

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Scheme 11: Examples of 6’-OH cinchona alkaloid catalyzed processes include: (a) Deng’s addition of dimethyl ma...

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Scheme 12: A diastereodivergent sulfa-Michael addition developed by Melchiorre and co-workers.

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Scheme 13: Melchiorre’s vinylogous Michael addition.

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Scheme 14: Simpkins’s TKP conjugate addition reactions.

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Scheme 15: Hydrocupreine catalyst HCPN-59 can be used in an asymmetric cyclopropanation.

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Scheme 16: The hydrocupreine and hydrocupreidine-based catalysts HCPN-65 and HCPD-67 demonstrate the potential...

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Scheme 17: Jørgensen’s oxaziridination.

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Scheme 18: Zhou’s α-amination using β-ICPD.

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Scheme 19: Meng’s cupreidine catalyzed α-hydroxylation.

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Scheme 20: Shi’s biomimetic transamination process for the synthesis of α-amino acids.

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Scheme 21: β-Isocupreidine catalyzed [4 + 2] cycloadditions.

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Scheme 22: β-Isocupreidine catalyzed [2+2] cycloaddition.

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Scheme 23: A domino reaction catalyst by cupreidine catalyst CPD-30.

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Scheme 24: (a) Dixon’s 6’-OH cinchona alkaloid catalyzed oxidative coupling. (b) An asymmetric oxidative coupl...

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Review

Published 07 Mar 2016

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