Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 3, Pages 720-724Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201307826
Keywords
aminomethoxysilanes; chiral siloxanes; diastereoselectivity; silicon; substitutions
Categories
Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
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A route towards the synthesis of N,O-functionalized silicon-stereogenic organosilanes with excellent optical purities has been developed. Investigations into the stereoconvergence and configurational stability of an aminomethoxysilane suggest a kinetically controlled multistep substitution mechanism. Selective exchange of the Si-N bond by a second Si-O bond builds the basis for the controlled formation of chiral siloxane units with different oxygen-containing functional groups. Subsequent reactions of the chiral aminomethoxysilanes with hydroxy groups support a general inversion mechanism at the asymmetrically substituted silicon atom of N,O-functionalized organosilanes.
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