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Addition of organometallic reagents to chiral N-methoxylactams: enantioselective syntheses of pyrrolidines and piperidines

Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compounds gave hemiaminals, which could be reduced...

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Main Authors: Jäkel, Mascha (Author) , Qu, Jianping (Author) , Schnitzer, Tobias (Author) , Helmchen, Günter (Author)
Format: Article (Journal)
Language:English
Published: 21 October 2013
In: Chemistry - a European journal
Year: 2013, Volume: 19, Issue: 49, Pages: 16746-16755
ISSN:1521-3765
DOI:https://doi.org/10.1002/chem.201302735
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/chem.201302735
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201302735
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Author Notes:Mascha Jäkel, Jianping Qu, Tobias Schnitzer, and Günter Helmchen

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520 |a Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compounds gave hemiaminals, which could be reduced diastereoselectively via acyliminium intermediates to give cis-piperidines or cis-pyrrolidines with substituents in the 2,6- or 2,5-positions, respectively. In addition, compounds with a quaternary carbon center could be synthesized by corresponding reactions with potassium cyanide/AcOH. The procedures were applied in the syntheses of alkaloids (−)-209D and (+)-prosophylline. 
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