期刊
ORGANIC LETTERS
卷 8, 期 17, 页码 3873-3876出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol061485k
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资金
- NIGMS NIH HHS [R01-GM69445] Funding Source: Medline
Catalytic hydrogenation of ethyl glyoxalate in the presence of 1,3-diynes 4a-9a using chirally modified rhodium catalysts enables formation of alpha-hydroxy esters 4c-9c in highly optically enriched form. Notably, for such trialkylsilyl-substituted 1,3-diynes, C-C coupling occurs exclusively at the carbon atom bearing silicon. pi-Back-bonding from low valent rhodium as described by the Dewar-Chatt-Duncanson model appears to direct the regiochemistry of C-C coupling, as corroborated by calculations of the diyne LUMO coefficients.
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