Asymmetric Synthesis of Enantiopure Pyrrolidines by C(sp3)−H Amination of Hydrocarbons

The asymmetric synthesis of enantiopure pyrrolidines is reported via a streamlined strategy relying on two sequential C−H functionalizations of simple hydrocarbons. The first step is a regio‐ and stereoselective catalytic nitrene C−H insertion. Then, a subsequent diastereoselective cyclization invol...

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Bibliographic Details
Published in:Angewandte Chemie 2021-09, Vol.133 (40), p.21876-21880
Main Authors: Lazib, Yanis, Retailleau, Pascal, Saget, Tanguy, Darses, Benjamin, Dauban, Philippe
Format: Article
Language:English
Subjects:
Amination
Asymmetric synthesis
Asymmetry
Chemical Sciences
Chemistry
C−H amination
haloamine
Hydrocarbons
nitrene
Organic chemistry
pyrrolidine
Stereoselectivity
Synthesis
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Summary:The asymmetric synthesis of enantiopure pyrrolidines is reported via a streamlined strategy relying on two sequential C−H functionalizations of simple hydrocarbons. The first step is a regio‐ and stereoselective catalytic nitrene C−H insertion. Then, a subsequent diastereoselective cyclization involving a 1,5‐hydrogen atom transfer (HAT) from a N‐centered radical leads to the formation of pyrrolidines that can then be converted to their free NH‐derivatives. Simple hydrocarbons such as alkanes are shown to be useful building blocks for the asymmetric synthesis of heterocycles. They are converted in only two steps to pyrrolidines by application of stereoselective C(sp3)−H amination reactions. Symmetrical and non‐symmetrical enantiopure 2,5‐disubstituted pyrrolidines are isolated in good yields.
ISSN:0044-8249
1433-7851
1521-3757
1521-3773
DOI:10.1002/ange.202107898