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Synlett 2001; 2001(8): 1225-1228
DOI: 10.1055/s-2001-16067
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Ring-Opening Allylation of Semicyclic N,O-Acetals Catalyzed by a Lewis Acid

Masaharu Sugiura* , Hiroyuki Hagio, Ryoji Hirabayashi, Shū Kobayashi
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax 3(5684)06 34; E-mail: skobayas@mol.f.u-tokyo.ac.jp
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Publication Date:
31 December 2001 (online)

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Ring-opening allylation of semicyclic N,O-acetals with allylic silanes is effectively catalyzed by a Lewis acid showing high diastereoselectivities. The synthetic utility of this method has been demonstrated in a stereoselective synthesis of an antimalarial agent, isofebrifugine.

semicyclic N,O-acetal - Lewis acid - allylation - stereoselective synthesis - antimalarial agent

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