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Synlett 1993; 1993(10): 759-760
DOI: 10.1055/s-1993-22599
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Copper Mediated Lithium Aluminum Hydride Reduction of Substituted Allylic Epoxides

J. F. Genus* , D. D. Peters, T. A. Bryson
  • *Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA
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Publication Date:
19 March 2002 (online)

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Copper-mediated lithium aluminum hydride reduction of 1-oxaspiro[2.5]oct-4-enes has been observed to primarily yield 1,4-products, although 1,2-products and general decomposition are encountered. Olefin substitution (α and β) affects the yield and selectivity. Alternate hydride coordination sites redirect reductive opening of these allylic epoxides.

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