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Synlett 2001; 2001(4): 0481-0484
DOI: 10.1055/s-2001-12333
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Highly Stereoselective Diels-Alder Reactions Achieved on Some Hexopyranosidic Templates

Takayuki Nagatsuka* , Shuhei Yamaguchi, Kiichiro Totani, Ken-ichi Takao, Kin-ichi Tadano
  • *Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan; Fax + 81-45-566-1571; E-mail: tadano@applc.keio.ac.jp
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Publication Date:
31 December 2001 (online)

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The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.

asymmetric synthesis - diastereoselectivity - Diels-Alder reaction - cyclopentadiene - norbornene derivatives