Reductive and Oxidative Transformations of the <i>N</i>‐(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines

Francois, David; Poupon, Erwan; Kunesch, Nicole; Husson, Henri‐Philippe

doi:10.1002/ejoc.200400404

Cited by 18 publications

(9 citation statements)

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“…An intermediary radical anion is formed and carries on to the decyanated product through the loss of CN – 22. Recently, Husson reported the reductive decyanation of α‐amino nitriles in the presence of Raney nickel under mild conditions 23. From a simple examination of these methods, it was clear that for technical convenience, NaBH 4 was the reactant of choice.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Alkaloids of Galipea officinalis by Alkylation of an α‐Amino Nitrile

et al. 2008

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A new synthetic approach directed towards the synthesis of naturally occurring 2-alkyl-tetrahydroquinolines is described. The C-C bonds in the α position relative to the nitrogen atom were formed by the reversal of the polarity of the C=N bond of α-amino nitrile 6, which was prepared electrochemically from 1-(phenylethyl)-tetrahydroquinoline. A NaBH 4 -mediated reductive decyanation process furnished benzylic amines 16a-d as mixtures of diastereomers (50-

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Section: Resultsmentioning

confidence: 99%

Synthesis of Alkaloids of Galipea officinalis by Alkylation of an α‐Amino Nitrile

et al. 2008

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“…More recently, the formation of alkyl metal species by reductive metallation has been developed. 8 Reductive decyanation and cyclization of the resulting organometallic intermediate was first described in Grierson’s synthesis of gephyrotoxin-16B ( 7 ) (eq. 3).…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Lepadiformine Alkaloids using N-Boc α-Amino Nitriles as Trianion Synthons

et al. 2012

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Lepadiformine A, B and C were synthesized in enantiomerically pure form using a reductive cyclization strategy. N-Boc α-amino nitriles were deprotonated and alkylated with enantiomerically pure dibromides to afford the first ring. The products were manipulated to introduce phosphate leaving-groups, and subsequent reductive lithiation followed by intramolecular alkylation formed the second ring with high stereoselectivity. The third ring was formed by intramolecular displacement of a mesylate by the deprotected amine. Lepadiformine A and B contain a hydroxymethyl group adjacent to the amine. This appendage was introduced in a sequence using a Polonovski-Potier reaction as the key step. The synthetic strategy is stereoselective and convergent, and demonstrates the utility of N-Boc α-amino nitriles as linchpins for alkaloid synthesis.

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“…The decyanation of α-aminonitriles with hydrogen present in an excess of Raney nickel was described by Husson and co-workers on oxazolidine derivatives [ 83 – 84 ]. The authors logically proposed that the decyanation occurred via the reduction of an iminium ion intermediate.…”

Section: Reviewmentioning

confidence: 99%

The reductive decyanation reaction: an overview and recent developments

Mattalia¹

2017

Beilstein J. Org. Chem.

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Reductive and Oxidative Transformations of the N‐(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines

Abstract: Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non-racemic N-(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process

Cited by 18 publications

References 56 publications

Synthesis of Alkaloids of Galipea officinalis by Alkylation of an α‐Amino Nitrile

Synthesis of Alkaloids of Galipea officinalis by Alkylation of an α‐Amino Nitrile

Total Synthesis of Lepadiformine Alkaloids using N-Boc α-Amino Nitriles as Trianion Synthons

The reductive decyanation reaction: an overview and recent developments

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