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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Bibliographic Details
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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Summary: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.
ISSN:0385-5414
1881-0942
DOI:10.3987/com-05-s(k)25