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Enantioselective Cobalt‐Catalyzed Intermolecular Hydroacylation of 1,6‐Enynes
Author(s) -
Whyte Andrew,
Bajohr Jonathan,
Torelli Alexa,
Lautens Mark
Publication year - 2020
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.202006716
Subject(s) - hydroacylation , enantioselective synthesis , stereocenter , domino , catalysis , chemistry , cobalt , stereochemistry , intermolecular force , bond cleavage , combinatorial chemistry , organic chemistry , aldehyde , molecule
We report a cobalt‐catalyzed hydroacylation of 1,6‐enynes with exogenous aldehydes in a domino sequence to construct enantioenriched ketones. The products were obtained in good yields with excellent regio‐, diastereo‐, and enantioselectivity. Furthermore, the chiral products served as valuable precursors to access complex spirocyclic scaffolds with three contiguous stereocenters. The asymmetric hydroacylation process exhibited no C−H crossover and no KIE, thus indicating that the C−H bond cleavage was not involved in the turnover‐limiting step.