RhII-Catalyzed Response of [alpha]-Diazocarbonyl Compounds Bearing [beta]-Trichloroacetylamino Substituent: C[bond]H Insertion versus 1,2-H Switch manage <<>>
Written by Zhenhua Zhang, Weifeng Shi, Jian Zhang, Bo Zhang, Bingge Liu, Yiyang Liu, Bo Fan, Fengping Xiao, Feng Xu, Jianbo Wang on December 10, 2009 – 1:46 pm -The RhII-carbene resistance is dramatically touched by the neighboring substituents. If the neighboring substituent is an OH group, a1,2-H get is the exclusive pathway. If it is an OAc group, a 1,2-acetoxy migration is observed. If it is p-toluenesulfonyl group, 1,3 and 1,5-C[bond]H insertion are the major pathways, and the 1,2-H squad is completely suppressed. If the adjacent substituent is a trichloroacetyl amino group, 1,5-C[bond]H insertion competes with the 1,2-hydride shift, and no 1,3-C[bond]H insertion can be observed. Both electronic and steric factors are ethical for the switching of the RhII-carbene resistance pathway. The quite stereoselective 1,5-C[bond]H insertions in RhII-catalyzed counterbalance of [alpha]-diazocarbonyl compounds, bearing [beta]-trichloroacetylamino substituent, can be utilized as a tale way to synthesize five-membered cyclic [beta]-amino acid derivatives <<>>
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