Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts

Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved. This method affords practical and efficient access to chiral 3-amino-3-phosphonyl-substituted oxindole derivatives in high yields with excellent enan...

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Published inBeilstein journal of organic chemistry Vol. 12; no. 1; pp. 1551 - 1556
Main Authors Jang, Hee Seung, Kim, Yubin, Kim, Dae Young
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 20.07.2016
Beilstein-Institut
Subjects
3-amino-3-phosphonyl-substituted oxindole
bifunctional organocatalyst
Chemistry
ketimines
Letter
organocatalysis
squaramide
α-aminophosphonates
organocatalysis
bifunctional organocatalyst
ketimines
α-aminophosphonates
squaramide
3-amino-3-phosphonyl-substituted oxindole
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Abstract Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved. This method affords practical and efficient access to chiral 3-amino-3-phosphonyl-substituted oxindole derivatives in high yields with excellent enantioselectivities (up to 99% ee).
AbstractList Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved. This method affords practical and efficient access to chiral 3-amino-3-phosphonyl-substituted oxindole derivatives in high yields with excellent enantioselectivities (up to 99% ee).
Summary Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved. This method affords practical and efficient access to chiral 3-amino-3-phosphonyl-substituted oxindole derivatives in high yields with excellent enantioselectivities (up to 99% ee).
Author Jang, Hee Seung
Kim, Yubin
Kim, Dae Young
AuthorAffiliation 1 Department of Chemistry, Soonchunhyang University, Soonchunhyang-Ro 22, Asan, Chungnam 31538, Korea
AuthorAffiliation_xml – name: 1 Department of Chemistry, Soonchunhyang University, Soonchunhyang-Ro 22, Asan, Chungnam 31538, Korea
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  givenname: Hee Seung
  surname: Jang
  fullname: Jang, Hee Seung
  organization: Department of Chemistry, Soonchunhyang University, Soonchunhyang-Ro 22, Asan, Chungnam 31538, Korea
– sequence: 2
  givenname: Yubin
  surname: Kim
  fullname: Kim, Yubin
  organization: Department of Chemistry, Soonchunhyang University, Soonchunhyang-Ro 22, Asan, Chungnam 31538, Korea
– sequence: 3
  givenname: Dae Young
  surname: Kim
  fullname: Kim, Dae Young
  organization: Department of Chemistry, Soonchunhyang University, Soonchunhyang-Ro 22, Asan, Chungnam 31538, Korea
BackLink https://www.ncbi.nlm.nih.gov/pubmed/27559405$$D View this record in MEDLINE/PubMed
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Issue 1
Keywords organocatalysis
bifunctional organocatalyst
ketimines
α-aminophosphonates
squaramide
3-amino-3-phosphonyl-substituted oxindole
Language English
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Snippet Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved. This...
Summary Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved....
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StartPage 1551
SubjectTerms 3-amino-3-phosphonyl-substituted oxindole
bifunctional organocatalyst
Chemistry
ketimines
Letter
organocatalysis
squaramide
α-aminophosphonates
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Title Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts
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https://search.proquest.com/docview/1814654419
https://pubmed.ncbi.nlm.nih.gov/PMC4979900
https://doaj.org/article/12b4fd633c5a4932a9d0f86400702763
Volume 12
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