Preparation of New Chiral Building Blocks: Highly Enantioselective Reduction of Prochiral 1,3-Cycloalkanediones Possessing a Methyl Group and a Protected Hydroxymethyl Group at Their C2 Position with Baker's Yeast or CBS Catalyst
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- Hideaki Watanabe
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1, Ohkubo, Shinjuku, Tokyo 169-8555, Japan
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- Mitsuhiro Iwamoto
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1, Ohkubo, Shinjuku, Tokyo 169-8555, Japan
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- Masahisa Nakada
- Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1, Ohkubo, Shinjuku, Tokyo 169-8555, Japan
書誌事項
- 公開日
- 2005-05-10
- DOI
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- 10.1021/jo050349a
- 公開者
- American Chemical Society (ACS)
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説明
Highly enantioselective reduction of five-, six-, seven-, and eight-membered prochiral 1,3-cycloalkanediones possessing a methyl group and a protected hydroxymethyl group at their C2 position with baker's yeast or CBS catalyst and a new efficient and general method for preparing the 1,3-cycloalkanediones have been developed. These baker's yeast mediated reductions were found to produce corresponding ketols with high optical purity (99% ee) and high yield. All of the prepared ketols and their derivatives, chiral building blocks, have been fully characterized, and their absolute configurations have been determined. These compounds would be useful for the convergent synthesis of complex natural products.
収録刊行物
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 70 (12), 4652-4658, 2005-05-10
American Chemical Society (ACS)
