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A new norephedrine-derived chiral base for epoxide rearrangement reactions

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JournalTetrahedron Letters
DatePublished - 26 Nov 1999
Issue number48
Volume40
Number of pages3
Pages (from-to)8423-8425
Original languageEnglish

Abstract

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. (C) 1999 Elsevier Science Ltd. All rights reserved.

    Research areas

  • diamines, epoxides, rearrangement, allylic alcohols, LITHIUM AMIDE, ENANTIOSELECTIVE DEPROTONATION, ASYMMETRIC-SYNTHESIS, MESO-EPOXIDES, DIAMINES, CATALYSTS, ALCOHOLS, OXIDES

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