Asymmetric nucleophilic addition to β- and γ-alkoxy aldehydes using carbohydrate as a chiral auxiliary
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Yoshida, T
[1
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Chika, J
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Tokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268502, JapanTokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268502, Japan
Chika, J
[1
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Takei, H
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Tokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268502, JapanTokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268502, Japan
Takei, H
[1
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[1] Tokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268502, Japan
The nucleophilic addition of Grignard reagents and allyltributyltin to chiral omega-tetrahydropyranyloxy propanal and butanal derived from L-fucose and D-arabinose gave the corresponding alcohols with high diastereoselectivity (up to 51% de by 1,6-asymmetric induction and 95% de by 1,5-asymmetric induction). (C) 1998 Elsevier Science Ltd. All rights reserved.