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Yb(OTf)3-Catalyzed 1,3-dipolar cycloaddition of nitrone with alkene; Switch in diastereoselectivity by solvent and bidentate auxiliary

✍ Scribed by Satoshi Minakata; Toshihiro Ezoe; Keiko Nakamura; Ilhyong Ryu; Mitsuo Komatsu

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 231 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01022-3

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✦ Synopsis

Yb(OTf)3 (ytterbium trifluoromethanesulfonate)-catalyzed diastereoselective 1,3dipolar cycloaddition of a nitrone with ct,13-unsaturated carbonyl compounds was studied. While endo-cycloadduct was obtained from the reaction of C, N-diphenylnitrone with N-crotonoyloxazolidinone or N-crotonyl-2-pyrrolidinone in toluene, exo-adduct was predominant in acetonitrile. The enones carrying imidazolidinone or succinimide ring reacted with the nitrone to give the exo-adducts primarily in both solvents.

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