Highly stereoselective addition of silylphosphines to chiral aldehydes

The reaction between diphenyl(trimethylsilyl)phosphine or bis(trimethylsilyl)phenylphosphine and chiral aldehydes proceeds with high stereoselectivity to give diastereomerically pure tertiary α-siloxyalkylphosphines. The reaction between diphenyl(trimethylsilyl)phosphine and chiral aldehydes proceed...

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Bibliographic Details
Published in:Tetrahedron letters 2004-09, Vol.45 (37), p.6955-6957
Main Authors: Kolodiazhnyi, Oleg I., Guliaiko, Irina V., Kolodiazhna, Anastasia O.
Format: Article
Language:English
Subjects:
Chiral aldehydes
Chiral α-trimethylsiloxyalkylphosphines
Silylphosphines
Stereoselectivity
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Summary:The reaction between diphenyl(trimethylsilyl)phosphine or bis(trimethylsilyl)phenylphosphine and chiral aldehydes proceeds with high stereoselectivity to give diastereomerically pure tertiary α-siloxyalkylphosphines. The reaction between diphenyl(trimethylsilyl)phosphine and chiral aldehydes proceeds with high stereoselectivity to give diastereomerically pure tertiary α-trimethylsiloxyalkylphosphines. The diastereomeric purity of the addition products was 90–100%. The products were purified via the formation of borane–phosphine complexes. The reaction of bis(trimethylsilyl)phenylphosphine with acetonide ( R)-glyceraldehyde provides tertiary bis(glyceryl)phosphines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.07.074