180322-79-6Relevant academic research and scientific papers
Asymmetric Rh(II)-catalyzed cyclopropanation of alkenes with diacceptor diazo compounds: P -methoxyphenyl ketone as a general stereoselectivity controlling group
Lindsay, Vincent N. G.,Nicolas, Cyril,Charette, Andre B.
supporting information; experimental part, p. 8972 - 8981 (2011/08/04)
Different diacceptor diazo compounds bearing an α-PMP-ketone group were found to be effective carbene precursors for the highly stereoselective Rh2(S-TCPTTL)4-catalyzed cyclopropanation of alkenes (EWG = NO2, CN, CO2Me). The resulting products were readily transformed into a variety of biologically relevant enantiopure molecules, such as cyclopropane α- and β-amino acid derivatives. Different mechanistic studies carried out led to a rationale for the high diastereo- and enantioselectivity obtained, where the PMP-ketone moiety was found to play a critical role in the stereoinduction process. Additionally, the use of catalytic amounts of achiral Lewis bases to influence the enantioinduction of the reactions developed is documented.
Experimental evidence for the all-up reactive conformation of chiral rhodium(II) carboxylate catalysts: Enantioselective synthesis of cis-cyclopropane α-amino acids
Lindsay, Vincent N. G.,Lin, Wei,Charette, Andre B.
supporting information; experimental part, p. 16383 - 16385 (2010/02/16)
(Chemical Equation Presented) Useful empirical insights onto the enantioinduction process of chiral Rh(II)-carboxylate catalysts are described in the first catalytic asymmetric cyclopropanation of alkenes with α-nitro diazoacetophenones. X-ray, solution N
Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
Davies, Huw M. L.,Bruzinski, Paul R.,Lake, Debra H.,Kong, Norman,Fall, Michael J.
, p. 6897 - 6907 (2007/10/03)
The rhodium N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes leads to a very general method for the synthesis of functionalized cyclopropanes in a highly diastereoselective and enantioselective mode. A det
