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Studies on organolithium-induced alkylative desymmetrisation of epoxides: synthesis of enantioenriched beta-amino cycloheptenols from 6,7-epoxy-8-azabicyclo[3.2.1]octanes

Abstract:

The synthesis and enantioselective α-deprotonation - double ring opening of 6,7-epoxy-8-azabicyclo[3.2.1]octanes 5 using organolithiums in the presence of (-)-sparteine or (4S)-2,2′-(1-ethylpropylidene)bis-4-(1- methylethyl)-4,5-dihydrooxazole, giving amino cycloheptenols in up to 85% yield and 82% ee is described. The impact of different reaction variables on reaction profiles has been studied, including the nature of organolithium, solvent, ligand, temperature and epoxide structure. The rea...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2004.04.047

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
TETRAHEDRON
Volume:
60
Issue:
24
Pages:
5185-5199
Publication date:
2004-06-07
DOI:
ISSN:
0040-4020
URN:
uuid:34b350ba-3691-4528-a678-8e393d87e6f7
Source identifiers:
39085
Local pid:
pubs:39085

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