22666-34-8Relevant academic research and scientific papers
(2R,1'S,2'R)- And (2S,1'S,2'R)-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines and their incorporation into hormaomycin analogues
De Meijere, Armin,Kozhushkov, Sergei I.,Yufit, Dmitrii S.,Grosse, Christian,Kaiser, Marcel,Raev, Vitaly A.
supporting information, p. 2844 - 2857 (2015/02/19)
Efficient and scalable syntheses of enantiomerically pure (2 R ,1' S ,2' R )- and (2 S ,1' S ,2' R )-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines 9a - c , as well as allo-D-threonine ( 4 ) and ( 2 S,3R)-β-methylphenylalanine (3), using the Belokon' approach with (S )- and (R )-2-[( N-benzylprolyl)amino]benzophenone [(S)- and (R)-10 ] as reusable chiral auxiliaries have been developed. Three new fluoromethyl analogues of the naturally occurring octadepsipeptide hormaomycin ( 1 ) with (fluoromethylcyclopropyl) alanine moieties have been synthesized and subjected to preliminary tests of their antibiotic activity.
Regioselectivity in the Ring Opening of 2-Alkylcyclopropylmethyl Radicals: the Effect of Electronegative Substituents
Ratier, Max,Pereyre, Michel,Davies, Alwyn G.,Sutcliffe, Roger
, p. 1907 - 1916 (2007/10/02)
The regioselectivity of the ring-opening of the trans-2-alkylcyclopropylmethyl radical A to give the primary alkyl radicals B, or the secondary alkyl radicals C, has been investigated, where the groups R and/or CXY carry electronegative substituents.All these reactions gave principally the secondary alkyl radicals C, whereas, in the absence of electronegative substituents, ring-opening occurs in favour of the primary alkyl radicals B.This regioselectivity is interpreted in terms of the frontier orbital interactions which are involved.
