Highly enantioselective Michael addition of silyl nitronates to α,β-unsaturated aldehydes catalyzed by designer chiral ammonium bifluorides: Efficient access to optically active γ-nitro aldehydes and their enol silyl ethers

Journal of the American Chemical Society

Volumn 125, Issue 30, 2003, Pages 9022-9023

  Ooi, Takashi ^a   Doda, Kanae ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; AMMONIUM DERIVATIVE; AMMONIUM HYDROGEN FLUORIDE; AMMONIUM NITRONATE; CARBONYL DERIVATIVE; CINNAMALDEHYDE; ENOL SILYL ETHER; GAMMA NITROALDEHYDE; NITRIC ACID DERIVATIVE; SILYL NITRONATE; TOLUENE; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYL NITRONATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DERIVATIZATION; DIASTEREOISOMER; ENANTIOMER; METHODOLOGY; MICHAEL ADDITION; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0041365865     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0352810     Document Type: Article

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26. Unfortunately, the catalytic and chiral efficiency of 1b was significantly decreased in toluene mainly due to its solubility problem.
27. For the purification, silanized silica gel purchased from Merck was used to minimize the protonation.
28. For details, see the Supporting Information.