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. 2021 Mar 19;23(6):2292-2297.
doi: 10.1021/acs.orglett.1c00420. Epub 2021 Mar 8.

Ligand-Controlled, Palladium-Catalyzed Asymmetric [4+4] and [2+4] Cycloadditions

Qiuyu Li  1 , Rui Pan  1 , Meihui Wang  1 , Hequan Yao  1 , Aijun Lin  1
Affiliations

Ligand-Controlled, Palladium-Catalyzed Asymmetric [4+4] and [2+4] Cycloadditions

Qiuyu Li et al. Org Lett. .

Abstract

Ligand-controlled, palladium-catalyzed asymmetric [4+4] and [2+4] cycloaddition reactions of benzofuran-derived azadienes have been developed. Taking advantage of chiral P,N-ligand (S,Rp)-PPFA, we obtained a variety of benzofuro[2,3-c][1,5] oxazocines in good yields with excellent enantioselectivities via [4+4] cycloaddition reactions. Employing chiral P,P-ligand (S)-Cl-MeO-BIPHEP, the chemo- and regioselectivities were switched to synthesize tetrahydropyran-fused spirocyclic compounds in good efficiency via [2+4] cycloaddition reactions.

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