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2005
Carboxylic amides
Q 0490
Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and
Transformation: One-Pot Sequential Catalytic Asymmetric Epoxida27- 090 Functional
tion-Regioselective Epoxide-Opening Process. — The use of a 1:1:1 complex derived from Sm(OiPr)3, (S)-BINOL and Ph3AsO as catalyst for the epoxidation of
α,β-unsaturated amides, and subsequent addition of TmsN3 to the reaction mixture
leads to smooth epoxide ring opening. anti-β-Azido-α-hydroxy amides are formed in
excellent overall yields with complete regioselectivity and excellent enantiomeric excesses. The key to the success of this sequential process is the in situ generation of a
highly reactive samarium azide complex through dynamic ligand exchange. Examination of sulfur and carbon nucleophiles instead of TmsN3 in the epoxide-ring opening
step as well as transformations of some ring-opened products into bioactive compounds
are also described. — (TOSAKI, S.-Y.; TSUJI, R.; OHSHIMA*, T.; SHIBASAKI, M.;
J. Am. Chem. Soc. 127 (2005) 7, 2147-2155; Grad. Sch. Pharm. Sci., Univ. Tokyo,
Bunkyo, Tokyo 113, Japan; Eng.) — Klein
2005
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