Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of [Rh(COD)Cl]2and TMS-CN under Almost Neutral Conditions
Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of [Rh(COD)Cl]<sub>2</sub>and TMS-CN under Almost Neutral Conditions
In the presence of a catalytic amount of a transition metal compound such as [Rh(COD)Cl]2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields. In the coexistence of catalytic amounts of [Rh(COD)Cl]2 and TMS-CN, silyl enol ethers or ketene silyl acetals react with acetals, aldehyes, or imines to yield the corresponding coupling products in good yields under almost neutral conditions.
A new catalyst trimethylsilyl bis(fluorosulfonyl)imide has been prepared for aldol type reactions and allylation of acetals. The catalyst has been found to be more active than trimethylsilyl triflate for the above reactions.