Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones
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作者:
Hirabayashi, R
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Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Hirabayashi, R
[1
]
Ogawa, C
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Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Ogawa, C
[1
]
Sugiura, M
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Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Sugiura, M
[1
]
Kobayashi, S
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Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, S
[1
]
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[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Allyltrichlorosilanes reacted with benzoylhydrazones in DMF without the use of any catalyst to afford the corresponding homoallylic benzoylhydrazines in good to high yields. The reactions proceeded at 0 degreesC to room temperature under mild conditions. In addition, it was found that the reactions tolerated well the steric hindrance of hydrazones and allyltrichlorosilanes. Indeed, ketone-derived benzoylhydrazones reacted with allyltrichlorosilane smoothly to afford the corresponding N'-tert-alkyl-N-benzoylhydrazines in high yields. In crotylation with (E)- and (Z)-crotyltrichlorosilanes, syn- and anti-adducts were stereospecifically obtained, respectively. These reactions. are most likely to proceed via a cyclic chairlike transition state where the R group takes an axial position. When alpha -heteroatom-substituted chiral benzoylhydrazones were used, high anti-diastereoselectivities were observed. These adducts can be readily converted to homoallylic amines in high yields without epimerization.
机构:
Univ Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, S
Hirabayashi, R
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Univ Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, Japan
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, S
Hasegawa, Y
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机构:Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Hasegawa, Y
Ishitani, H
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机构:Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
机构:
Univ Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, S
Hirabayashi, R
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机构:
Univ Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Japan Sci & Technol Corp, CREST, Grad Sch Pharmaceut Sci,Bunkyo Ku, Tokyo 1130033, Japan
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, S
Hasegawa, Y
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机构:Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan
Hasegawa, Y
Ishitani, H
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机构:Univ Tokyo, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp, CREST,Bunkyo Ku, Tokyo 1130033, Japan