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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903365
Subject(s) - enantiopure drug , kinetic resolution , allylic rearrangement , stereocenter , diastereomer , allene , rhodium , chemistry , enantiomer , catalysis , stereochemistry , organic chemistry , enantioselective synthesis
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.