Rhodium‐Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3‐Diketones | Zendy

Hilpert Lukas J. | Zendy; Breit Bernhard | Zendy

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Rhodium‐Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3‐Diketones

Author(s) -

Hilpert Lukas J.,

Breit Bernhard

Publication year - 2019

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201903365

Subject(s) - enantiopure drug , kinetic resolution , allylic rearrangement , stereocenter , diastereomer , allene , chemistry , rhodium , enantiomer , stereochemistry , catalysis , enantioselective synthesis , organic chemistry

A rare case of a parallel kinetic resolution of racemic 1,3‐disubstituted allenes by means of a rhodium‐catalyzed addition to 1,3‐diketones furnishing enantiopure allylic 1,3‐diketones is described. Mechanistic experiments demonstrate that the different allene enantiomers react in parallel to either the diastereomeric E ‐ or Z ‐allylic 1,3‐diketones with the same absolute configuration of the newly formed stereogenic center. A broad substrate scope demonstrates the synthetic utility of this new method.

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