Efficient approach for the design of effective chiral quaternary phosphonium salts in asymmetric conjugate additions
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作者:
Shirakawa, Seiji
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机构:Kyoto Univ, Grad Sch Sci, Dept Chem, Lab Synthet Organ Chem,Sakyo Ku, Kyoto 6068502, Japan
Shirakawa, Seiji
Kasai, Atsuyuki
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机构:Kyoto Univ, Grad Sch Sci, Dept Chem, Lab Synthet Organ Chem,Sakyo Ku, Kyoto 6068502, Japan
Kasai, Atsuyuki
Tokuda, Takashi
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机构:Kyoto Univ, Grad Sch Sci, Dept Chem, Lab Synthet Organ Chem,Sakyo Ku, Kyoto 6068502, Japan
Tokuda, Takashi
Maruoka, Keiji
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机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Lab Synthet Organ Chem,Sakyo Ku, Kyoto 6068502, JapanKyoto Univ, Grad Sch Sci, Dept Chem, Lab Synthet Organ Chem,Sakyo Ku, Kyoto 6068502, Japan
Maruoka, Keiji
[1
]
机构:
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Lab Synthet Organ Chem,Sakyo Ku, Kyoto 6068502, Japan
PHASE-TRANSFER CATALYSTS;
ALPHA-AMINO-ACIDS;
BOC-PROTECTED OXINDOLES;
HYDROGEN-BONDING SITE;
ENANTIOSELECTIVE SYNTHESIS;
MICHAEL ADDITION;
AMMONIUM-SALTS;
3-SUBSTITUTED OXINDOLES;
TRANSFER ALKYLATION;
ORGANOCATALYSIS;
D O I:
10.1039/c3sc22130j
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
An efficient approach for the design of chiral quaternary phosphonium bromides as chiral phase-transfer catalysts was demonstrated. A catalyst library of phosphonium salts with various structures was readily constructed using commercially available chiral phosphines as catalyst precursors, and an optimized catalyst was successfully applied to highly enantioselective conjugate additions under base-free phase-transfer conditions with low catalyst loading.