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Synlett 2000; 2000(7): 0979-0982
DOI: 10.1055/s-2000-6685
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Highly Stereoselective Lewis Acid Mediated Conjugate Radical Additions to Methyl α-d-Glucopyranoside Derivatives Tethering an Unsaturated Ester Moiety at C-4

Ryosuke Munakata* , Kiichiro Totani, Ken-ichi Takao, Kin-ichi Tadano
  • *Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan; Fax +81-45-5 66-15 71; E-mail: tadano@applc.keio.ac.jp
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Publication Date:
31 December 2000 (online)

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The Lewis acid mediated conjugate additions of alkyl radicals to some 4-crotonyl derivatives of methyl α-d-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β-chiral butanoic ester.

asymmetric synthesis - conjugate additions - radical reactions - carbohydrates

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