Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams

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概要

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• Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides (1,4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH_4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2-naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et_3SiH) and trifluoroacetic acid (CF_3CO_2H) gave chiral bicyclic lactams (14,15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14,15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16,17) in high optical purity.

• 社団法人日本薬学会の論文
• 1994-01-15

著者

• 石田 昭彦

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 松木 健司

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 井上 博純

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 日野 亨

  千葉大 薬

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 中川 昌子

  千葉大 薬

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 松木 健司

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 井上 博純

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .

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