Catalytic asymmetric C-N bond formation: Phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates

Rylan J. Lundgren; Ashraf Wilsily; Nicolas Marion; Cong Ma; Ying Kit Chung; Gregory C. Fu

doi:10.1002/anie.201208957

Catalytic asymmetric C-N bond formation: Phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates

Rylan J. Lundgren, Ashraf Wilsily, Nicolas Marion, Cong Ma, Ying Kit Chung, Gregory C. Fu

Research output: Journal article publication › Journal article › Academic research › peer-review

112 Citations (Scopus)

Abstract

Pin the amine on the gamma: A new method has been developed for the γ-addition of nitrogen nucleophiles to γ-substituted alkynoates or allenoates through intra- and intermolecular processes that are catalyzed by spirophosphine 1 (see scheme). An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,β- unsaturated carbonyl compounds.

Original language	English
Pages (from-to)	2525-2528
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	9
DOIs	https://doi.org/10.1002/anie.201208957
Publication status	Published - 25 Feb 2013
Externally published	Yes

Keywords

amination
asymmetric catalysis
heterocycles
organocatalysis
phosphanes

ASJC Scopus subject areas

Catalysis
Chemistry(all)

More information

10.1002/anie.201208957

Cite this

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abstract = "Pin the amine on the gamma: A new method has been developed for the γ-addition of nitrogen nucleophiles to γ-substituted alkynoates or allenoates through intra- and intermolecular processes that are catalyzed by spirophosphine 1 (see scheme). An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,β- unsaturated carbonyl compounds.",

keywords = "amination, asymmetric catalysis, heterocycles, organocatalysis, phosphanes",

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Catalytic asymmetric C-N bond formation: Phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates. / Lundgren, Rylan J.; Wilsily, Ashraf; Marion, Nicolas et al.
In: Angewandte Chemie - International Edition, Vol. 52, No. 9, 25.02.2013, p. 2525-2528.

Research output: Journal article publication › Journal article › Academic research › peer-review

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AU - Lundgren, Rylan J.

AU - Wilsily, Ashraf

AU - Marion, Nicolas

AU - Ma, Cong

AU - Chung, Ying Kit

AU - Fu, Gregory C.

PY - 2013/2/25

Y1 - 2013/2/25

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KW - amination

KW - asymmetric catalysis

KW - heterocycles

KW - organocatalysis

KW - phosphanes

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DO - 10.1002/anie.201208957

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JO - Angewandte Chemie - International Edition

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Catalytic asymmetric C-N bond formation: Phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates

Abstract

Keywords

ASJC Scopus subject areas

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