Dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)piperidinonate] as a chiral Lewis acid: Catalytic enantioselective aldol reactions of acetate-derived silylketene acetals and aldehydes

A first example of chiral dirhodium(II) complex-catalyzed enantioselective Mukaiyama aldol reactions is described. The aldol addition reaction of methyl acetate-derived trimethylsilylketene acetal with specific aldehydes such as benzyloxyacetaldehyde and electron-poor aromatic aldehydes is effective...

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Published inHeterocycles Vol. 66; pp. 567 - 578
Main Authors Washio, T, Nakamura, S, Anada, M, Hashimoto, S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 31.12.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MUKAIYAMA-ALDOL
COMPLEX
ASYMMETRIC-SYNTHESIS
DIELS-ALDER REACTIONS
ESTER DERIVATIVES
asymmetric catalysis
KETENE
aldo reaction
enantioselection
sily ketne acetal
SILYL ENOL ETHERS
dirhodium(II) complex
GLYOXYLATE
ADDITIONS
C-H INSERTION
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Abstract A first example of chiral dirhodium(II) complex-catalyzed enantioselective Mukaiyama aldol reactions is described. The aldol addition reaction of methyl acetate-derived trimethylsilylketene acetal with specific aldehydes such as benzyloxyacetaldehyde and electron-poor aromatic aldehydes is effectively catalyzed by dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)piperidinonate] (1a), providing silylated aldol adducts in up to 94% ee.
AbstractList A first example of chiral dirhodium(II) complex-catalyzed enantioselective Mukaiyama aldol reactions is described. The aldol addition reaction of methyl acetate-derived trimethylsilylketene acetal with specific aldehydes such as benzyloxyacetaldehyde and electron-poor aromatic aldehydes is effectively catalyzed by dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)piperidinonate] (1a), providing silylated aldol adducts in up to 94% ee.
Author Washio, T
Hashimoto, S
Anada, M
Nakamura, S
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  surname: Anada
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  surname: Hashimoto
  fullname: Hashimoto, S
  email: hsmt@pharm.hokudai.ac.jp
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Cites_doi 10.1002/anie.200453821
10.1021/ja034993n
10.1073/pnas.0307025101
10.1055/s-2003-43351
10.1021/cr0200217
10.1021/ja047597t
10.1021/ol026488l
10.1021/ol0267127
10.1021/ja015692l
10.1002/adsc.200404245
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Keywords MUKAIYAMA-ALDOL
COMPLEX
ASYMMETRIC-SYNTHESIS
DIELS-ALDER REACTIONS
ESTER DERIVATIVES
asymmetric catalysis
KETENE
aldo reaction
enantioselection
sily ketne acetal
SILYL ENOL ETHERS
dirhodium(II) complex
GLYOXYLATE
ADDITIONS
C-H INSERTION
Language English
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  text: 2005-12-31
  day: 31
PublicationDecade 2000
PublicationPlace OXFORD
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PublicationTitle Heterocycles
PublicationTitleAbbrev HETEROCYCLES
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Snippet A first example of chiral dirhodium(II) complex-catalyzed enantioselective Mukaiyama aldol reactions is described. The aldol addition reaction of methyl...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)piperidinonate] as a chiral Lewis acid: Catalytic enantioselective aldol reactions of acetate-derived silylketene acetals and aldehydes
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