TY - JOUR
T1 - Synthesis of α-trifluoromethyl α-amino acids with aromatic, heteroaromatic and ferrocenyl subunits in the side chain
AU - Burger, K.
AU - Hennig, L.
AU - Tsouker, P.
AU - Spengler, J.
AU - Albericio, F.
AU - Koksch, B.
PY - 2006/7
Y1 - 2006/7
N2 - 5-Benzyloxy-4-trifluoromethyl-1,3-oxazoles, obtained from 5-fluoro-4-trifluoromethyloxazoles and benzyl alcohols, are capable for rearrangements. A 1,3 shift of a benzyl group is the key step of a new general route toward α-trifluoromethyl substituted aromatic and heteroaromatic amino acids, demonstrating that 5-fluoro-4-trifluoromethyl-1,3-oxazole is a synthetic Tfm-Gly equivalent. On reaction with benzpinacol partially fluorinated oxazoles are transformed into bis(trifluoromethyl) substituted 2,5-diamino adipic acid and N-benzoyl-2-benzhydryl-3,3,3-trifluoroalanine.
AB - 5-Benzyloxy-4-trifluoromethyl-1,3-oxazoles, obtained from 5-fluoro-4-trifluoromethyloxazoles and benzyl alcohols, are capable for rearrangements. A 1,3 shift of a benzyl group is the key step of a new general route toward α-trifluoromethyl substituted aromatic and heteroaromatic amino acids, demonstrating that 5-fluoro-4-trifluoromethyl-1,3-oxazole is a synthetic Tfm-Gly equivalent. On reaction with benzpinacol partially fluorinated oxazoles are transformed into bis(trifluoromethyl) substituted 2,5-diamino adipic acid and N-benzoyl-2-benzhydryl-3,3,3-trifluoroalanine.
KW - α-Trifluoromethylamino acids
KW - 1,3-Benzyl group migration versus Claisen rearrangement
KW - 5-Fluoro-4-trifluoromethyl-1,3-oxazoles
KW - Nucleophilic heteroaromatic substitution
KW - Synthetic Tfm-Gly equivalent
UR - http://www.scopus.com/inward/record.url?scp=33746147774&partnerID=8YFLogxK
U2 - 10.1007/s00726-006-0322-1
DO - 10.1007/s00726-006-0322-1
M3 - Artículo
C2 - 16715413
AN - SCOPUS:33746147774
SN - 0939-4451
VL - 31
SP - 55
EP - 62
JO - Amino Acids
JF - Amino Acids
IS - 1
ER -