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2005
Ring opening reactions
O 0132
Scandium—Bipyridine-Catalyzed Enantioselective Addition of Alcohols and
to meso-Epoxides. — The first catalytic enantioselective addition of aliphatic
07- 037 Amines
alcohols (II) to meso-epoxides (I) is presented using a Sc(O-Tf)3—chiral bipyridine
complex as catalyst. The reaction affords mono-protected anti-diols (III) in high yields
and selectivities for aryl-substituted epoxides. The novel catalytic complex is successfully applied to the enantioselective addition of amines (IV) to meso-epoxides and
gives N-protected amino alcohols (V) in comparably high yields and selectivities. —
(SCHNEIDER*, C.; SREEKANTH, A. R.; MAI, E.; Angew. Chem., Int. Ed. 43
(2004) 42, 5691-5694; Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany;
Eng.) — Mischke
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