Merging Alkene Isomerization Enables Difunctionalization of Cyclic Enamines toward Ring-Fused Aminal Synthesis

Licheng Wu; Jingping Qu; Yifeng Chen

doi:10.1021/acs.orglett.3c00094

Merging Alkene Isomerization Enables Difunctionalization of Cyclic Enamines toward Ring-Fused Aminal Synthesis

Org Lett. 2023 Feb 17;25(6):992-997. doi: 10.1021/acs.orglett.3c00094. Epub 2023 Feb 6.

Authors

Licheng Wu¹, Jingping Qu¹, Yifeng Chen¹

Affiliation

¹ Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.

PMID: 36746651
DOI: 10.1021/acs.orglett.3c00094

Abstract

Here we report a Pd-catalyzed isomerization of alicyclic allyl amine to achieve the unprecedented α,β-difunctionalization of synthetically inaccessible trisubstituted cyclic enamine. The dual role of in situ formed enamine intermediate allows for the intermolecular formal [4 + 2] reaction with acrylamide or isatoic anhydride to simultaneously construct the C-C bond and C-N bond, thus realizing the expedient construction of [4.3.0]-aminal with excellent diastereoselectivity and high atom economy.