Iron and Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions between Nitrones and Enals

The single coordination-site transition metal Lewis acids [CpM(BIPHOP-F)][SbF6] (M = Fe, Ru) catalyze the [3+2] dipolar cycloaddition reaction between reactive nitrones and α,β-unsaturated aldehydes to give chiral isoxazolidines with ee values of 75 to >96%. The stereochemistry of the major enant...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-05, Vol.124 (18), p.4968-4969
Main Authors: Viton, Florian, Bernardinelli, Gérald, Kündig, E. Peter
Format: Article
Language:English
Subjects:
Acrolein - analogs & derivatives
Acrolein - chemistry
Catalysis
Chemistry
Exact sciences and technology
Iron - chemistry
Isoxazoles - chemical synthesis
Models, Molecular
Nitrogen Oxides - chemistry
Organic chemistry
Organometallic Compounds - chemistry
Ruthenium - chemistry
Stereoisomerism
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Summary:The single coordination-site transition metal Lewis acids [CpM(BIPHOP-F)][SbF6] (M = Fe, Ru) catalyze the [3+2] dipolar cycloaddition reaction between reactive nitrones and α,β-unsaturated aldehydes to give chiral isoxazolidines with ee values of 75 to >96%. The stereochemistry of the major enantiomer is consistent with an endo approach of the nitrone to the Cα-Si-face of the enal in the s-trans conformation in the (R,R)-catalyst site. The absolute configuration is based on an X-ray structure determination.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja017814f