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Synlett 1993; 1993(10): 795-797
DOI: 10.1055/s-1993-22613
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Diastereoselective Alkylations of t-Butyl Glycolate Ether Enolates

Steven J. Wittenberger* , Steven A. Boyd, William R. Baker
  • *Process Chemistry, D-45L/AP10, Abbott Laboratories, Pharmaceutical Products Division, Abbott Park, Illinois 60064, USA
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Publication Date:
19 March 2002 (online)

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Lithium enolates derived from t-butyl glycolate ethers possessing oxygen-containing functional groups which were capable of chelating the lithium counter-ion were alkylated with benzyl bromide. Diastereoselectively in the alkylation reaction ranged from 1:1 to 1:10. A bicyclo[3.3.0] enolate structure is proposed to account for these observations.