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From Stereochemistry of Functionalized Organosilicon Compounds towards Organolithium Chemistry - Jonathan Bauer

My main research interests include the synthesis, reactivity and application of optically pure silicon-chiral aminomethoxysilanes, deprotonation reactions in the periphery of complex functionalized chiral silanes as well as the mechanistic insight into the stereochemical course of substitution reactions.

As a consequence of our studies on the one-step substitution of silicon-bonded methoxy groups by lithium amides,[1] we introduced a chiral directing group (–NR2*) in our starting compounds which allows a highly stereoselective substitution reaction leading to aminomethoxysilanes of type A.

fig1

Furthermore, stereocontrolled deprotonation of a methylene group next to silicon[2] paves the way to complex building blocks (B) with multiple chirality centers.

fig2b

[1] J. O. Bauer, C. Strohmann, Chem. Commun. 2012, 48, 7212-7214.

[2] a) C. Strohmann, B. C. Abele, K. Lehmen, D. Schildbach, Angew. Chem. 2005, 117, 3196-3199; Angew. Chem. Int. Ed. 2005, 44, 3136-3139; b) H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911.