74124-68-8Relevant academic research and scientific papers
Asymmetric conjugate reductions with samarium diiodide: Asymmetric synthesis of (2S,3R)- And (2S,3S)-[2-2H,3-2H]-leucine-(S)- phenylalanine dipeptides and (2S,3R)-[2-2H,3-2H]- phenylalanine methyl ester
Davies, Stephen G.,Rodriguez-Solla, Humberto,Tamayo, Juan A.,Cowley, Andrew R.,Concellon, Carmen,Garner, A. Christopher,Parkes, Alastair L.,Smith, Andrew D.
, p. 1435 - 1447 (2007/10/03)
The highly diastereoselective samarium diiodide and D2O-promoted conjugate reduction of homochiral (E)- and (Z)-benzylidene and isobutylidene diketopiperazines (E)-5,7 and (Z)-6,8 has been demonstrated. This methodology allows the asymmetric synthesis of methyl (2S,3R)-dideuteriophenylalanine 27 in ≥95% de and >98% ee, and (2S,3R)- or (2S,3S)-dideuterioleucine-(S)- phenylalanine dipeptides 37 and 38 in moderate de, 66% and 74% respectively. A mechanism is proposed to account for this process. The Royal Society of Chemistry 2005.
Stereo-divergent synthesis of L-threo- and L-erythro-[2,3-2H2]amino acids using optically active dioxopiperazine as a chiral template
Oba, Makoto,Terauchi, Tsutomu,Qwari, Yuki,Imai, Yoko,Motoyama, Izumi,Nishiyama, Kozaburo
, p. 1275 - 1281 (2007/10/03)
A stereo-divergent synthesis of L-threo- and L-erythro-[2,3-2H2]amino acids from the same chiral auxiliary is described. Aldolization of N,N′-di(tert-butoxycarbonyl)dioxopiperazine 2, derived from L-valine, with various aldehydes followed by successive elaboration gives various 2,3-dehydroamino acid derivatives. Catalytic deuteriation of the derivatives then followed by acidic hydrolysis affords L-[2,3-2H2]amino acids in good yields with high optical purities. It becomes clear that diastereoselective deuteriation for either the threo or the erythro isomer depends upon the protective groups on the nitrogen atoms in the dioxopiperazine ring.
Substituent-dependent asymmetric synthesis of L-threo- and L-erythro-[2,3-2H2]phenylalanine from chiral (Z)-dehydrophenylalanine
Oba, Makoto,Nakajima, Shinji,Nishiyama, Kozaburo
, p. 1875 - 1876 (2007/10/03)
A stereo-divergent synthesis of L-threo- and L-erythro-[2,3-2H2]-phenylalanine by a catalytic deuteriation of (Z)-dehydrophenylalanine included in a chiral diketopiperazine ring is accomplished simply by changing the substituents on the nitrogen atoms in the diketopiperazine ring.
