1,2-vinyl and 1,2-acetylenyl migration in Rh(II) carbene reaction: remarkable bystander effect.
A series of beta-(trichloroacetyl)amino alpha-diazo carbonyl compounds have been synthesized, and their Rh(II)-catalyzed reaction was investigated. 1,2-Migration was the predominant reaction pathway, and the migratory aptitude was found to be dramatically affected by the beta-substituents. The 1,2-vinyl and 1,2-acetylenyl group migration occurs preferentially in the presence of beta-hydrogen in Rh(2)(OAc)(4)-catalyzed reaction of beta-(trichloroacetyl)amino alpha-diazo carbonyl compounds. A possible reaction mechanism is discussed.
Shi
Weifeng
W
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Xiao
Fengping
F
Wang
Jianbo
J