Unprecedented Ligand Dependent SN2′ Mechanism on the Palladium-catalyzed Nucleophilic Substitution to Bicyclic Dienyl Acetates

Unprecedented Ligand Dependent SN2′ Mechanism on the Palladium-catalyzed Nucleophilic Substitution to Bicyclic Dienyl Acetates

Palladium-catalyzed nucleophilic reaction to bicyclic dienyl acetates 1 was studied with both optically active substrates and deuterium labeled substrates in order to clarify regioselectivity of the reaction. The regioselectivity depended on phosphine ligands. Thus, SN2 type reaction was observed us...

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Veröffentlicht in:Chemistry letters 2005-03, Vol.34 (3), p.408-409
Hauptverfasser: Daimon, Hisashi, Kitamura, Takahiro, Kawahara, Tamotsu, Shimizu, Isao
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container_title Chemistry letters
container_volume 34
creator Daimon, Hisashi
Kitamura, Takahiro
Kawahara, Tamotsu
Shimizu, Isao
description Palladium-catalyzed nucleophilic reaction to bicyclic dienyl acetates 1 was studied with both optically active substrates and deuterium labeled substrates in order to clarify regioselectivity of the reaction. The regioselectivity depended on phosphine ligands. Thus, SN2 type reaction was observed using PPh3. Whereas, unprecedented SN2′ type reaction proceeded in high yields using DPPP and DPPB, which is applicable to a remote nucleophilic substitution.
doi_str_mv 10.1246/cl.2005.408
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title Unprecedented Ligand Dependent SN2′ Mechanism on the Palladium-catalyzed Nucleophilic Substitution to Bicyclic Dienyl Acetates
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