Enantioselective synthesis of (+)(R)- and (–)(S)-nicotine based on Ir-catalysed allylic amination

Welter, Carolin; Moreno, Rosa M.; Streiff, Stéphane; Helmchen, Günter

doi:10.1039/b508634e

Cited by 75 publications

(31 citation statements)

References 21 publications

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“…Iridium catalyzed N-allylations of hydrazines [680]. An iridium catalyzed N-allylation was used in a synthesis of (+)-and (−)-nicotine [681]. Rhenium catalyzed N-propargylation of amines with propargylic alcohols [682].…”

Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…[562] Also is the case, the ring-closure metathesis is successful only with the pyridinium salt. In a diimine reduction with tosylhydrazine, the double bond can be reduced while preserving the Cbz-protecting group.…”

Section: Nicotinementioning

confidence: 98%

Pharmaceuticals

Schaefer

2014

Natural Products in the Chemical Industry

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A boy who is born in Germany today has a probable life expectancy of around 77 years, and a girl one of 82 years -twice as long as in the year 1880. This increase is a consequence of both, better living circumstances -working conditions, food, clothing, housing -, and also a result of more comprehensive medical care. Thus, a whole range of infectious diseases has been wiped out, or brought at least under control, and the mortality rate for civilisation-and age-related diseases has dropped. Vaccinations and drugs play a key role in this outcome. The 20th century is characterised especially by the worldwide blossoming of the pharmaceutical industry. More and more, the targeted search for and development of new drugs have replaced serendipitous discoveries (Fig. 5.1). Pharmaceuticals of the last century.

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“…(13) is one of the many piperidine and pyrrolidine alkaloids isolated from the leaves of Nicotaiana tabacum. Welter and coworkers developed a synthesis route where 13 was obtained in only four steps from pyridinylallyl carbonate 10 involving RCM (Scheme 2.4) [17]. The synthesis commenced with an Ir-catalyzed asymmetric allylic amination of 10 to produce bis-alkene 11 in excellent enantiomeric purity when using phosphoramidate ligand L1.…”

Section: Dihydropyrrolesmentioning

confidence: 99%

“…The skeletons of all these alkaloids feature the tropinone moiety, produced by oxidation and subsequent cyclization of (+)-hygrine (17) [19]. It was envisioned that RCM could be invoked in order to develop an enantioselective synthesis of 17 [20].…”

Section: Pyrrolidines (−)-(S)-nicotinementioning

confidence: 99%

Natural Products Containing Medium‐Sized Nitrogen Heterocycles Synthesized by Ring‐Closing Alkene Metathesis

Broek

Meeuwissen

Delft

et al. 2010

Metathesis in Natural Product Synthesis

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The formation of carbon-carbon bonds is a crucial issue in organic synthesis. Out of all methodologies available, the metathesis reaction has, over the past decade, evolved as one of the most useful tools in this field to rapidly construct the skeleton of carba-and heterocyclic molecules [1]. Key step of the metathesis reaction entails the metal-catalyzed redistribution of two carbon-carbon double bonds by a scission-recombination process [2]. Among various applications of the metathesis reaction, ring-closing metathesis (RCM) has emerged as one of the most powerful tools for the construction of natural and unnatural cyclic compounds (Scheme 2.1) [3]. Other types of metathesis reactions developed so far include cross-metathesis (CM), ring-opening metathesis (ROM), ring rearrangement metathesis (RRM, combining ROM with RCM in a tandem sequence), and ene-yne metathesis [3].The metathesis reaction has already been used for several decades in polymer chemistry for ring-opening metathesis polymerization (ROMP) [4]. Only since the development of well-defined molybdenum and ruthenium carbene complexes by Schrock [5] and Grubbs [6] in 1990 and 1992, respectively, an explosion of their application in organic synthesis has been witnessed. Initially, it was demonstrated that the Schrock catalyst [Mo]-I could serve as a homogeneous catalyst for olefin RCM [7]. Unfortunately, metal carbene complex [Mo]-

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Enantioselective synthesis of (+)(R)- and (–)(S)-nicotine based on Ir-catalysed allylic amination

Abstract: The synthesis of nicotine with enantiomeric excess of >99% ee was accomplished by asymmetric Ir-catalysed allylic amination followed by ring closing metathesis and racemization-free double bond reduction.

Cited by 75 publications

References 21 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Pharmaceuticals

Natural Products Containing Medium‐Sized Nitrogen Heterocycles Synthesized by Ring‐Closing Alkene Metathesis

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