Construction of a Chiral Silicon Center by Rhodium‐Catalyzed Enantioselective Intramolecular Hydrosilylation |
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Authors: | Dr Yuki Naganawa Tomoya Namba Mayu Kawagishi Prof?Dr Hisao Nishiyama |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464‐8603 (Japan) |
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Abstract: | Rhodium‐catalyzed enantioselective desymmetrizing intramolecular hydrosilylation of symmetrically disubstituted hydrosilanes is described. The original axially chiral phenanthroline ligand (S)‐BinThro (Binol‐derived phenanthroline) was found to work as an effective chiral catalyst for this transformation. A chiral silicon stereogenic center is one of the chiral motifs gaining much attention in asymmetric syntheses and the present protocol provides cyclic five‐membered organosilanes incorporating chiral silicon centers with high enantioselectivities (up to 91 % ee). The putative active RhI catalyst takes the form of an N,N,O‐tridentate coordination complex, as determined by several complementary experiments. |
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Keywords: | asymmetric catalysis desymmetrization hydrosilylation rhodium silicon |
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