Catalytic Enantioselective Synthesis of Key Intermediates for Triazole Antifungal Agents
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- Masato Suzuki
- Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, and PRESTO, Japan Science and Technology Corporation, Japan
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- Nobuki Kato
- Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, and PRESTO, Japan Science and Technology Corporation, Japan
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- Motomu Kanai
- Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, and PRESTO, Japan Science and Technology Corporation, Japan
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- Masakatsu Shibasaki
- Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, and PRESTO, Japan Science and Technology Corporation, Japan
書誌事項
- 公開日
- 2005-06-01
- DOI
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- 10.1021/ol050398+
- 公開者
- American Chemical Society (ACS)
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説明
[reaction: see text] A short-step synthesis of versatile chiral building blocks for triazole antifungal agents such as ZD0870 and Sch45450 was developed via catalytic enantioselective cyanosilylation of electron-deficient ketones as the key step. High enantioselectivity was produced using a catalyst prepared from Gd(HMDS)(3) and ligand 5 in a 2:3 ratio. This new catalyst preparation method was superior to the previous method using Gd(O(i)Pr)(3) as a metal source. A rationale for the difference is proposed on the basis of structural studies of the catalyst complexes using ESI-MS.
収録刊行物
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- Organic Letters
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Organic Letters 7 (13), 2527-2530, 2005-06-01
American Chemical Society (ACS)