Abstract
AbstractThe cyclization of δ‐acetoxy‐O‐allyl‐ and ϵ‐acetoxy‐O‐homoallyl‐trichloroacetimidates to 4‐vinyloxazolines and a 4‐vinyldihydrooxazine has been efficiently achieved by olefin aminopalladation–β‐heteroatom elimination. (Z)‐Allylic imidates bearing a secondary δ‐acetoxy group underwent PdII‐catalysed cyclization to give the E isomers of 4‐vinyloxazolines selectively and gave no Overman rearrangement products. Using a chiral substrate, it has been demonstrated that cyclization to 4‐vinyloxazolines occurs with high chirality transfer. Stereoselective E isomer formation and chirality transfer provided a basis from which to discuss the possible reaction mechanism. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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