Palladium‐Catalyzed Dienylations of Chelated Enolates | Zendy

Basak Sankar | Zendy; Kazmaier Uli | Zendy

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Palladium‐Catalyzed Dienylations of Chelated Enolates

Author(s) -

Basak Sankar,

Kazmaier Uli

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800519

Subject(s) - chemistry , isomerization , chirality (physics) , chelation , palladium , catalysis , allylic rearrangement , product distribution , reaction mechanism , organic chemistry , stereochemistry , medicinal chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark

Isomerization‐free reactions of dienyl carbonates with chelated amino acid ester enolates at –78 °C provide important information concerning the mechanism of these dienylations. The formation of regioisomeric products can be explained by competing S N 2/S N 2′ reactions, and the product distribution can be influenced by the proper choice of the reaction conditions. Chiral allylic substrates show a significant transfer of chirality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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