TY - JOUR
T1 - Concise Synthesis of Enantiomerically Pure (1'S,2'R)- and (1'R,2'S)-2S-Amino-3-(2'-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-l-lysine
AU - Altamore, Timothy
AU - Nguyen, Oanh
AU - Churches, Quentin
AU - Cavanagh, Kate
AU - Nguyen, Xuan
AU - Duggan, Sandhya
AU - Krippner, Guy
AU - Duggan, Peter
PY - 2013
Y1 - 2013
N2 - A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl- cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.
AB - A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl- cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.
UR - http://www.scopus.com/inward/record.url?scp=84884199926&partnerID=8YFLogxK
U2 - 10.1071/CH13309
DO - 10.1071/CH13309
M3 - Article
SN - 0004-9425
VL - 66
SP - 1105
EP - 1111
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 9
ER -