Catalytic Enantioselective Amide Allylation of Isatins and Its Application in the Synthesis of 2-Oxindole Derivatives Spiro-Fused to the α-Methylene-γ-Butyrolactone Functionality
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Takahashi, Masaki
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Shizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, JapanShizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Takahashi, Masaki
[1
]
Murata, Yusuke
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Shizuoka Univ, Grad Sch Sci & Technol, Naka Ku, Hamamatsu, Shizuoka 4328561, JapanShizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Murata, Yusuke
[2
]
Yagishita, Fumitoshi
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Chiba Univ, Dept Appl Chem & Biotechnol, Grad Sch Engn, Inage Ku, Chiba 2638522, JapanShizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Yagishita, Fumitoshi
[3
]
Sakamoto, Masami
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Chiba Univ, Dept Appl Chem & Biotechnol, Grad Sch Engn, Inage Ku, Chiba 2638522, JapanShizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Sakamoto, Masami
[3
]
Sengoku, Tetsuya
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Shizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, JapanShizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Sengoku, Tetsuya
[1
]
Yoda, Hidemi
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Shizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Shizuoka Univ, Grad Sch Sci & Technol, Naka Ku, Hamamatsu, Shizuoka 4328561, JapanShizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
Yoda, Hidemi
[1
,2
]
机构:
[1] Shizuoka Univ, Grad Sch Engn, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
[2] Shizuoka Univ, Grad Sch Sci & Technol, Naka Ku, Hamamatsu, Shizuoka 4328561, Japan
[3] Chiba Univ, Dept Appl Chem & Biotechnol, Grad Sch Engn, Inage Ku, Chiba 2638522, Japan
This article is a full account of the work exploring the potential utility of catalytic enantioselective amide allylation of various isatins using indium-based chiral catalysts. A survey of various isatin substrates and NH-containing stannylated reagents revealed that the reaction has a remarkably wide scope to result in extremely high yields and enantioselectivities (up to > 99 %, 99% ee) of variously substituted homoallylic alcohols. Several mechanistic investigations demonstrated that the substrate-reagent hydrogen-bond inter-action plays a critical role in the formation of the key transition states to result in enhanced catalytic reaction. The success of this approach allowed convenient access to chiral 2-oxindoles spiro-fused to the alpha-methylene-gamma-butyrolactone functionality and their halogenated derivatives in almost enantiopure forms, thus highlighting the general utility of this synthetic method to deliver a large variety of antineoplastic drug candidates and pharmaceutically meaningful compounds.
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页码:11091 / 11100
页数:10
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[1]
[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206