Synthetic elaboration of the side chain of (R)-2, 2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: a new regio-and stereoselective strategy to δ-functionalized β …

…, A Mordini, M Caracciolo

Index: Reginato, Gianna; Mordini, Alessandro; Caracciolo, Massimo Journal of Organic Chemistry, 1997 , vol. 62, # 18 p. 6187 - 6192

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Citation Number: 63

Abstract

An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)- ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an ...

~80%

~4%

~0%

~59%

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