1034147-48-2Relevant 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.
Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(-)-bornyl malonate
Bagnoli, Luana,Scarponi, Catalina,Testaferri, Lorenzo,Tiecco, Marcello
body text, p. 1506 - 1514 (2009/12/01)
The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane α-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described.
