Preparation of the Zinc Enolate Equivalent of Amides by Zinciomethylation of Isocyanates: Catalytic Asymmetric Reformatsky-Type Reaction

作者：Haraguchi Ryosuke; Matsubara Seijiro^*

来源：Synthesis (Germany), 2014, 46(17): 2272-2282.

DOI：10.1055/s-0034-1378514

• organozinc reagents
• dizinc compounds
• Reformatsky reaction
• asymmetric synthesis
• catalysis

Bis(iodozincio)methane [ CH2(ZnI)(2)] transforms isocyanates (R-N=C=O) into the enolate equivalent of amides via zinciomethylation. The reactivity of the enolate equivalent as a nucleophile toward aldehydes depends on the R group of the isocyanate. For the enolate equivalent formed from phenyl isocyanate, the addition of a catalytic amount of an optically active amino alcohol, which acts as an activator, leads to a catalytic asymmetric Reformatsky-type reaction.

• 出版日期2014-9