Synthesis and Development of Novel Main Group Element Compounds having Tin-based Steric Protection Group

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In recent years there has been much interest in the reactive main group element compounds having an efficient steric protection group because of their unique chemical properties. Although many successes and developments of the steric protection groups have been reported, the central atom has been limited to carbon in many cases. In this research project, we have been investigating on the tin-based steric protection groups for the kinetic stabilization of reactive functional groups. For example, tris(9-triptycyl)stannyl group (Trp_3Sn-) has been shown as an effective steric protection group for-SOH function. Also, we synthesized and investigated on the related compounds bearing three 9,10-dihydro-9,10-ethenoanthracen-l-yl (Dbb) groups on a central tin atom (Dbb_3Sn-) as a novel tin-based steric protection group. Also, the synthesis and functionalization of methylbis(9-triptycyl)stannyl group (Trp_2MeSn-) has been studied.Moreover, static and dynamic stereochemistry of several Trp3Sn-compounds were studied. X-ray crystallography of the Trp3SnX (X= hologenes, alkyl groups) showed that the three Trp goups meshed with each other like bevel gears and formed near-C3 chiral conformation. In solution, the process of enantiomerization of those Trp3SnX compounds has been investigated by VT-NMR method.