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2005
Pyrrole derivatives
R 0120
Stereoselective Synthesis of Highly Substituted ∆1-Pyrrolines: exo-Selective
1,3-Dipolar Cycloaddition Reactions with Azlactones. — A highly diastereoselec06- 115 tive and efficient synthesis of highly substituted ∆1-pyrroline-5-carboxylic acid derivatives is reported. It involves the Ag(I)-catalyzed [3 + 2] cycloaddition reaction of
muenchnones derived from oxazolinones with alkenes. Under the reaction conditions,
no isomerization of the generated ∆1-pyrrolines and no decarboxylation to the corresponding pyrroles occurs. Pyrroline (IVa) undergoes ring-opening upon exposure to
nucleophiles to give trans-products (VI) and (VIII). — (PEDDIBHOTLA, S.; TEPE*,
J. J.; J. Am. Chem. Soc. 126 (2004) 40, 12776-12777; Dep. Chem., Mich. State Univ.,
East Lansing, MI 48824, USA; Eng.) — Klein
2005
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