55285-80-8Relevant articles and documents
Catalytic asymmetric intramolecular homologation of ketones with α-diazoesters: Synthesis of cyclic α-Aryl/Alkyl β-ketoesters
Li, Wei,Tan, Fei,Hao, Xiaoyu,Wang, Gang,Tang, Yu,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 1608 - 1611 (2015/01/30)
A catalytic asymmetric intramolecular homologation of simple ketones with α-diazoesters was firstly accomplished with a chiral N,N′-dioxide-Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α-aryl/alkyl β-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl- and alkyl-substituted ketone groups reacted with α-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β-ketoesters in high yield and enantiomeric excess.
α-Arylation by rearrangement: On the reaction of enolates with diaryliodonium salts
Norrby, Per-Ola,Petersen, Tue B.,Bielawski, Marcin,Olofsson, Berit
supporting information; experimental part, p. 8251 - 8254 (2010/10/18)
Surprising equilibration: A new mechanism for the title reaction is supported by DFT calculations and experimental observations. The C-I and OI intermediates are isoenergetic and equilibrate quickly. Thus, any chiral information induced in the initial complex will be destroyed. In the final CC bond-forming step, a [2,3]-rearrangement from the O-I bonded intermediate is slightly preferred over the [1,2]elimination from the C-I bonded isomer (see scheme). (Figure Presented)
The direct acyl-alkylation of arynes
Tambar, Uttam K.,Stoltz, Brian M.
, p. 5340 - 5341 (2007/10/03)
An efficient and mild acyl-alkylation of arynes is described. The method is used to synthesize medium-sized carbocycles by the ring-expansion of cyclic β-ketoesters. Copyright
