180322-85-4Relevant academic research and scientific papers
Application of chiral sulfides to catalytic asymmetric aziridination and cyclopropanation with in situ generation of the diazo compound
Aggarwal, Varinder K.,Alonso, Emma,Fang, Guangyu,Ferrara, Marco,Hynd, George,Porcelloni, Marina
, p. 1433 - 1436 (2007/10/03)
Imines and alkenes can be converted into the corresponding aziridines and cyclopropanes (see scheme, PTC = phase-transfer catalyst, Ts = toluene-4-sulfonyl) in good yield with moderate to high d.r. and high ee values using tosylhydrazone salts with catalytic quantities of chiral sulfide (5-20 mol%) and metal catalyst (1 mol%). The process is particularly suited to the synthesis of conformationally locked cyclopropyl amino acids, which can now be prepared in only three steps from commercially available material in 100% ee.
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
