STEREO-DIVERGENT SYNTHESIS OF L-THREO-[2,3-H-2(2)]AMINO AND L-ERYTHRO-[2,3-H-2(2)]AMINO ACIDS USING OPTICALLY-ACTIVE DIOXOPIPERAZINE AS A CHIRAL TEMPLATE
M. Oba et al., STEREO-DIVERGENT SYNTHESIS OF L-THREO-[2,3-H-2(2)]AMINO AND L-ERYTHRO-[2,3-H-2(2)]AMINO ACIDS USING OPTICALLY-ACTIVE DIOXOPIPERAZINE AS A CHIRAL TEMPLATE, Journal of the Chemical Society. Perkin transactions. I, (7), 1998, pp. 1275-1281
A stereo-divergent synthesis of L-three-and L-erythro-[2,3-H-2(2)]amin
o acids from the same chiral auxiliary is described. Aldolization of N
,N'-di(tert-butoxycarbonyl)dioxopiperazine 2, derived from L-valine, w
ith various aldehydes followed by successive elaboration gives various
2,3-dehydroamino acid derivatives. Catalytic deuteriation of the deri
vatives then followed by acidic hydrolysis affords L-[2,3-H-2(2)]amino
acids in good yields with high optical purities, It becomes clear tha
t diastereoselective deuteriation for either the three or the erythro
isomer depends upon the protective groups on the nitrogen atoms in the
dioxopiperazine ring.