6-Aminopenicillanic acid (6-APA) and two of its derivatives, 6-APA benzyl ester (6-APA-OBn) and Penicillin G (PenG), have been evaluated as catalysts for use in direct cross-aldol reactions in different solvents and mixtures. The effects of catalyst loading, reaction time, pH and temperature on the yield and stereoselectivity have been studied, 6-APA proved to be an effective catalyst in terms of yield for the reaction between cyclohexanone and p-nitrobenzaldehyde, especially in neat conditions. The stereoselectivity of the reaction was conditioned by the presence of two competing mechanisms: one an imine-enamine pathway and the other a Bronsted acid catalysis. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Hayashi, Yujiro
Kojima, Masahiro
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Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Kojima, Masahiro
Yasui, Yusuke
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Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Yasui, Yusuke
Kanda, Yuta
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Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Kanda, Yuta
Mukaiyama, Takasuke
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Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Mukaiyama, Takasuke
Shomura, Hiroki
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Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Shomura, Hiroki
Nakamura, Daichi
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Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Nakamura, Daichi
Ritmaleni
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机构:Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
Ritmaleni
Sato, Itaru
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Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, JapanTohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
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Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanTokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Hayashi, Yujiro
Aratake, Seiji
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Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanTokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Aratake, Seiji
Okano, Tsubasa
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Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanTokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Okano, Tsubasa
Takahashi, Junichi
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Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanTokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Takahashi, Junichi
Sumiya, Tatsunobu
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Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanTokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Sumiya, Tatsunobu
Shoji, Mitsuru
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Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanTokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
机构:
Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R ChinaChinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Gao, Qiang
Liu, Yan
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Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R ChinaChinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Liu, Yan
Lu, Sheng-Mei
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Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R ChinaChinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Lu, Sheng-Mei
Li, Jun
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Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R ChinaChinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
Li, Jun
Li, Can
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Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R ChinaChinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China