The Journal of organic chemistry

Cerium (III) chloride-mediated reactions of sulfonamide dianions

DC Johnson, TS Widlanski

Index: Johnson II, David C.; Widlanski, Theodore S. Journal of Organic Chemistry, 2003 , vol. 68, # 13 p. 5300 - 5309

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Citation Number: 28

Abstract

Presented here is the first report on the ability of cerium (III) chloride to mediate high-yielding and, oftentimes, highly diastereoselective additions of N-benzyl-α, N-dilithio methanesulfonamide to aldehydes and ketones of biological importance. Smooth addition was effected to base-sensitive substrates such as Fmoc-protected alaninal, citral, 5- cholesten-3-one, uridine 5'-aldehyde, 3'-ketouridine, and 3'-ketothymidine. The reaction ...