Rhodium‐Catalyzed Enantioselective Defluorinative α‐Arylation of Secondary Amides

Young Jin Jang, Daniel Rose, Bijan Mirabi, Mark Lautens

doi:10.1002/anie.201808509

Rhodium‐Catalyzed Enantioselective Defluorinative α‐Arylation of Secondary Amides

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Young Jin Jang

Davenport Research Laboratories Department of Chemistry University of Toronto Toronto Ontario M5S 3H6 Canada
Daniel Rose

Davenport Research Laboratories Department of Chemistry University of Toronto Toronto Ontario M5S 3H6 Canada
Bijan Mirabi

Davenport Research Laboratories Department of Chemistry University of Toronto Toronto Ontario M5S 3H6 Canada
Mark Lautens

Davenport Research Laboratories Department of Chemistry University of Toronto Toronto Ontario M5S 3H6 Canada

書誌事項

公開日: 2018-11-08

権利情報

http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.201808509

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>We exploited the reactivity of an electronically biased Michael acceptor to perform a defluorinative α‐arylation reaction using a chiral diene(L*)‐rhodium catalyst. Through this methodology, we are able to obtain various secondary amides, containing a tertiary α‐stereocenter and a β,γ‐unsaturated <jats:italic>gem</jats:italic>‐difluoro olefin, with excellent enantioselectivities. This methodology addresses the limitations of the previously described α‐arylation methods to construct stereo‐labile tertiary α‐stereocenters. Further investigation of the reaction via in situ <jats:sup>19</jats:sup>F NMR monitoring suggests that the formation of the product leads to the inhibition of the active rhodium catalyst.</jats:p>