TY - JOUR
T1 - Facile deuteration of chiral N,N'-substituted piperazines
AU - Santes, V.
AU - Gómez, E.
AU - Santillan, R.
AU - Farfán, N.
PY - 2001
Y1 - 2001
N2 - The synthesis of four chiral N,N'-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD4 or BD3·THF to afford 2,3-d2-piperazine and 2,3-dimethyl-2,3-d2-piperazine, while 2,2,3,3-d4- and 2,2,3,3,5,6-d6-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.
AB - The synthesis of four chiral N,N'-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD4 or BD3·THF to afford 2,3-d2-piperazine and 2,3-dimethyl-2,3-d2-piperazine, while 2,2,3,3-d4- and 2,2,3,3,5,6-d6-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.
KW - Amino alcohols
KW - Asymmetric synthesis
KW - Bisoxazolidine
KW - Condensation
KW - N,N'-substituted piperazine
KW - Reductions
UR - http://www.scopus.com/inward/record.url?scp=0035125831&partnerID=8YFLogxK
U2 - 10.1055/s-2001-10810
DO - 10.1055/s-2001-10810
M3 - Artículo
SN - 0039-7881
SP - 235
EP - 238
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 2
ER -