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Cyclization of Trichloroacetimidates by Olefin Aminopalladation β-Heteroatom Elimination

✍ Scribed by Ansis Maleckis; Ieva Jaunzeme; Aigars Jirgensons

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
313 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

The 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 Pd II -catalysed cyclization to give the E isomers of 4-vinyloxazolines selectively and gave no Overman rearrangement products.

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