Tetrahedron

Highly stereoselective cycloadditions of Danishefsky's diene to (−)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

…, MJ Alves, A Goth, ML do Vale, JE Rodríguez-Borges

文献索引：Garcia-Mera, Xerardo; Alves, Maria J.; Goth, Albertino; Do Vale, Maria Luisa; Rodriguez-Borges, Jose E. Tetrahedron, 2013 , vol. 69, # 14 p. 2909 - 2919

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被引用次数: 5

摘要

Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels–Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)-or N-(R)-1-phenylethyl and (−)-8-phenylmenthyl or (+)-8- phenylneomenthyl. Adducts were formed in good yields (78–81%), with complete ...