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Synthesis 1992; 1992(12): 1261-1264
DOI: 10.1055/s-1992-26353
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Stereoselective One-Pot Method for the Introduction of an Amino Group to a Cyclohexane Ring. Preparation of the Octahydroisobenzofuro[7a,1-d]oxazole Ring System

Kenji Saito* , Hideo Takagi, Makoto Yamamoto, Kazutoshi Yamada
  • *Graduate School of Science and Technology, Chiba University, 1-33 Yayoi-cho, Chiba-shi, 260 Japan and Organic Synthesis Laboratory, Nippon Soda Co. LTD., 345 Takada, Odawara-shi, Kanagawa Pref., 250-02 Japan
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Publication Date:
29 April 2002 (online)

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Stereoselective one-pot synthesis of octahydroisobenzofuro[7a,1-d]-oxazole-2,5-diones 7-14 via base-catalyzed addition-cyclization reaction of hydroxy lactones 4a-4d with various isocyanates 5a-5f is described. The ring system contains diastereoselectively regulated three contiguous asymmetric carbons.