Journal of the American Chemical Society

Highly enantioselective and diastereoselective Ireland-Claisen rearrangement of achiral allylic esters

EJ Corey, DH Lee

Index: Corey; Lee, Duck-Hyung Journal of the American Chemical Society, 1991 , vol. 113, # 10 p. 4026 - 4027

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Citation Number: 124

Abstract

" Reaction times at-20 OC: 14 days for entries I, 2, 5, 7, and 8; 7 days for entries 3, 4, and 6. bDiastereomeric ratios determined by GC analysis of benzyl (entry 1) or methyl esters (entries 3-6) or by'H NMR analysis of benzyl ester (entry 2). CEe values determined after reductioin to the corresponding primary alcohol and conversion to the MTPA ester by'H NMR (entries 1-5, 7, and 8)(see: Dale, JA; Mosher, HSJ Am. Chem. SOC. 1973, 95, 512-519) or ...