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Enantioselective Rhodium-Catalyzed Pauson-Khand Reactions of 1,6-Chloroenynes with 1,1-Disubstituted Olefins

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Title
Enantioselective Rhodium-Catalyzed Pauson-Khand Reactions of 1,6-Chloroenynes with 1,1-Disubstituted Olefins
Author(s)
Ylagan, Ridge Michael P.; Eric Jaewon Lee; Negru, Daniela E.; Ricci, Paolo; Bohyun Park; Haram Ryu; Mu-Hyun Baik; Evans, P. Andrew
Publication Date
2023-06
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.62, no.23
Publisher
WILEY-V C H VERLAG GMBH
Abstract
An enantioselective rhodium(I)-catalyzed Pauson-Khand reaction (PKR) using 1,6-chloroenynes that contain challenging 1,1-disubstituted olefins is described. In contrast to the previous studies with these types of substrates, which are only suitable for a single type of tether and alkyne substituent, the new approach results in a more expansive substrate scope, including carbon and heteroatom tethers with polar and non-polar substituents on the alkene. DFT calculations provide critical insight into the role of the halide, which pre-polarizes the alkyne to lower the barrier for metallacycle formation and provides the proper steric profile to promote a favorable enantiodetermining interaction between substrate and chiral diphosphine ligand. Hence, the chloroalkyne enables the efficient and enantioselective PKR with 1,6-enynes that contain challenging 1,1-disubstituted olefins, thereby representing a new paradigm for enantioselective reactions involving 1,6-enynes.
URI
https://pr.ibs.re.kr/handle/8788114/13682
DOI
10.1002/anie.202300211
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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