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Catalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular ?-addition of nitrogen nucleophiles to allenoates and alkynoates.

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

SUBMITTER: Lundgren RJ 

PROVIDER: S-EPMC3819219 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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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 RJ   Wilsily Ashraf A   Marion Nicolas N   Ma Cong C   Chung Ying Kit YK   Fu Gregory C GC  

Angewandte Chemie (International ed. in English) 20130121 9

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. An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,β-unsaturated carbonyl compounds. ...[more]

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