TY - JOUR
T1 - Asymmetric conjugate reductions with samarium diiodide
T2 - 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
AU - Davies, Stephen G.
AU - Rodríguez-Solla, Humberto
AU - Tamayo, Juan A.
AU - Cowley, Andrew R.
AU - Concellón, Carmen
AU - Garner, A. Christopher
AU - Parkes, Alastair L.
AU - Smith, Andrew D.
PY - 2005/4/21
Y1 - 2005/4/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=18444385349&partnerID=8YFLogxK
U2 - 10.1039/b500566c
DO - 10.1039/b500566c
M3 - Article
C2 - 15827639
AN - SCOPUS:18444385349
SN - 1477-0520
VL - 3
SP - 1435
EP - 1447
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 8
ER -