Carbenoid insertions into the siliconhydrogen bond catalyzed by chiral copper (I) schiff base complexes

✍ Scribed by Les A. Dakin; Scott E. Schaus; Eric N. Jacobsen; James S. Panek

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 213 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02013-9

✦ Synopsis

An asymmetric insertion reaction of ct-diazoesters derived from methyl arylacetates into the silicon-hydrogen bond of silanes was achieved using a copper (I) catalyst associated with a chiral, (72 symmetric Schiff base. Addition of the diazcesters 1 (1 equiv) to the Cu*Lig complex (R,R)-3 (0.1 equiv) in the presence of the silane reagent (1.5 equiv) at -40 ° C yielded the colTesponding insertion products 2 or 4 in good yields with varying levels of selectivity (up to 84% ee).