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Synlett 1996; 1996(8): 751
DOI: 10.1055/s-1996-5538
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Diastereoselective Introduction of Carbon Chain to Pyrrolidone Derivatives

Kentaro Sato, Tsukasa Koga, Keiichi Masuya, Keiji Tanino, Isao Kuwajima*
  • *Department of Chemistry, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
31 December 2000 (online)

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An ene reaction of cyclic N-acyliminium salts to introduce carbon side-chain in highly stereoselective manner was developed. Under the influence of TMSOTf, N-benzyl-5-benzoyloxy-2-pyrrolidone was treated with (Z)-2-(methylthio)crotyl silyl ether to give anti adduct in 96:4 diastereoselectivity. An enantioselective ene reaction was also achieved by using a chiral pyrrolidone derivative prepared from (R)-1-amino-1-phenyl-2-methoxyethane.

ene reaction - vinyl sulfide - imine - pyrrolizidine - pyrrolidine

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