Palladium-catalyzed decarboxylative allylation of vinyloxazolidin-2-ones with sodium sulfinates: stereoselective assembly of highly functionalized (Z)-allylic amines - Details

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We　report　a　general　approach　to　highly　functionalized　(Z)-allylic　amines　by　decarboxylative　allylation　of　vinyloxazolidin-2-ones.　This　process　engages　sodium　sulfinates　as　nucleophiles　to　form　a　new　carbon-sulfur　bond,　utilizing　a　palladium　catalyst　generated　from　Pd(OAc)2　and　diphosphine　ligand　dpppe.　The　scope　of　the　protocol　is　illustrated　by　the　synthesis　of　30　representative　allylic　amines　with　high　regio-　and　stereoselectivity.　Mechanistic　studies　show　that　the　Z-selectivity　of　the　reaction　stems　from　the　formation　of　a　palladacycle　intermediate　through　Pd-N　chelation.　The　synthetic　utility　of　this　method　was　further　exemplified　by　the　gram-scale　synthesis　and　subsequent　transformations　to　various　compounds.　©　2023　The　Royal　Society　of　Chemistry.

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[ 1 ] [Zhou L.]College of Chemistry, Fuzhou University, Fuzhou, 350102, China
[ 2 ] [Zhou L.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai, 200433, China
[ 3 ] [Zhou L.]Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai, 200433, China
[ 4 ] [Liu D.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai, 200433, China
[ 5 ] [Liu D.]Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai, 200433, China
[ 6 ] [Huang H.]College of Chemistry, Fuzhou University, Fuzhou, 350102, China
[ 7 ] [Huang H.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai, 200433, China
[ 8 ] [Huang H.]Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai, 200433, China
[ 9 ] [Zhang K.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai, 200433, China
[ 10 ] [Zhang K.]Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai, 200433, China
[ 11 ] [Ning Y.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai, 200433, China
[ 12 ] [Ning Y.]Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai, 200433, China
[ 13 ] [Chen F.-E.]College of Chemistry, Fuzhou University, Fuzhou, 350102, China
[ 14 ] [Chen F.-E.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai, 200433, China
[ 15 ] [Chen F.-E.]Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai, 200433, China

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Chemical Communications

ISSN： 1359-7345

Year： 2023

Issue： 65

Volume： 59

Page： 9892-9895

4 . 3

JCR@2023

4 . 3 0 0

JCR@2023

ESI HC Threshold：39

JCR Journal Grade：2

CAS Journal Grade：3

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ESI Highly Cited Papers on the List： 0 Unfold All

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