TY - JOUR
T1 - Dehydrative cyclization of serine, threonine, and cysteine residues catalyzed by molybdenum(VI) oxo compounds
AU - Sakakura, Akira
AU - Kondo, Rei
AU - Umemura, Shuhei
AU - Ishihara, Kazuaki
N1 - Funding Information:
This project was supported by JSPS.KAKENHI (Grant 20245022), the Toray Science Foundation, and the G-COE in Chemistry, Nagoya University.
PY - 2009/3/7
Y1 - 2009/3/7
N2 - Commercially available molybdenum(VI) oxides such as (NH4)2MoO4, (NH4)6Mo7O24·4H2O, MoO2(acac)2, and MoO2(TMHD)2 are highly effective dehydrative cyclization catalysts for the synthesis of a variety of oxazolines. The reaction proceeds with a complete retention of configuration at the β-position. For the dehydrative cyclization of cysteine derivatives, bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) shows remarkable catalytic activity and gives thiazolines without a significant loss of stereochemical integrity at the C2-exomethine positions.
AB - Commercially available molybdenum(VI) oxides such as (NH4)2MoO4, (NH4)6Mo7O24·4H2O, MoO2(acac)2, and MoO2(TMHD)2 are highly effective dehydrative cyclization catalysts for the synthesis of a variety of oxazolines. The reaction proceeds with a complete retention of configuration at the β-position. For the dehydrative cyclization of cysteine derivatives, bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) shows remarkable catalytic activity and gives thiazolines without a significant loss of stereochemical integrity at the C2-exomethine positions.
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U2 - 10.1016/j.tet.2008.12.074
DO - 10.1016/j.tet.2008.12.074
M3 - Article
AN - SCOPUS:59249084553
SN - 0040-4020
VL - 65
SP - 2102
EP - 2109
JO - Tetrahedron
JF - Tetrahedron
IS - 10
ER -