36147-17-8Relevant articles and documents
Stereoselective synthesis of silicon-stereogenic aminomethoxysilanes: Easy access to highly enantiomerically enriched siloxanes
Bauer, Jonathan O.,Strohmann, Carsten
, p. 720 - 724 (2014)
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. Broad access to silicon-stereogenic N,O-functionalized organosilanes in optically pure form is provided by a highly chemo- and diastereoselective substitution on aminodimethoxysilanes. The novel compounds could be further transformed stereoselectively with alcohols and a silanol and are predestined as building blocks for a controlled development of chiral siloxane units. Copyright
