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2004
Aziridine derivatives
R 0040
General Catalytic Synthesis of Highly Enantiomerically Enriched Terminal
from Racemic Epoxides. — The multistep route to N-sulfonylated termi45- 119 Aziridines
nal aziridines involves the indirect kinetic resolution of racemic oxiranes with sulfonamides. A highly selective hydrolytic kinetic resolution is followed by ring-opening of
the unreactive enantiomer by the sulfonamide promoted by the same catalyst. The resulting highly enantioenriched 1,2-amino alcohols [cf. (III)] are further converted to the
target aziridines by removal of the N-Boc group, O-mesylation, and cyclization (to be
continued). — (KIM, S. K.; JACOBSEN*, E. N.; Angew. Chem., Int. Ed. 43 (2004)
30, 3952-3953; Dep. Chem. Chem. Biol., Harvard Univ., Cambridge, MA 02138,
USA; Eng.) — Klein
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