Enantioselective synthesis of α-fluoro-β3-amino esters: synthesis of enantiopure, orthogonally protected α-fluoro-β3-lysine

PJ Duggan, M Johnston, TL March

Index: Duggan, Peter J.; Johnston, Martin; March, Taryn L. Journal of Organic Chemistry, 2010 , vol. 75, # 21 p. 7365 - 7372

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Citation Number: 15

Abstract

The scope of a tandem conjugate addition− fluorination sequence performed on α, β- unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(α- methylbenzyl) amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, α-fluoro-β3-amino esters can be obtained in up to quantitative yield and 80: 20 to> 99: 1 dr. This simple methodology does not rely on the ...

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