Tetrahedron Letters p. 8423 - 8425 (1999)
Update date:2022-08-16
Topics:
De Sousa, Simon E.
O'Brien, Peter
Steffens, H. Christian
The conversion of (1R,2S)-norephedrine into a novel chiral diamine (83% yield, simple two step synthesis) and its use as a chiral base in two epoxide rearrangement reactions is reported. Rearrangement of a 4,5-disubstituted cyclohexene oxide and of a 4-aminosubstituted cyclopentene oxide generated allylic alcohols of >90% ee. These results represent the highest levels of enantioselectivity reported to date for such substrates.
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