We thank the Deutsche Forschungsgemeinschaft for financial support and Wacker Chemie AG for providing us with special chemicals. J.O.B. thanks the Fonds der Chemischen Industrie for a Chemiefonds Fellowship and the Elitenetzwerk Bayern for scientific mentoring programs.
Stereoselective Synthesis of Silicon-Stereogenic Aminomethoxysilanes: Easy Access to Highly Enantiomerically Enriched Siloxanes†
Article first published online: 2 DEC 2013
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 3, pages 720–724, January 13, 2014
How to Cite
Bauer, J. O. and Strohmann, C. (2014), Stereoselective Synthesis of Silicon-Stereogenic Aminomethoxysilanes: Easy Access to Highly Enantiomerically Enriched Siloxanes. Angew. Chem. Int. Ed., 53: 720–724. doi: 10.1002/anie.201307826
- Issue published online: 8 JAN 2014
- Article first published online: 2 DEC 2013
- Manuscript Received: 5 SEP 2013
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
- chiral siloxanes;
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.