α-Nitrogenated organolithium compounds from α-amidomethyl and α-aminomethyl sulfones

DA Alonso, E Alonso, C Nájera, DJ Ramón, M Yus

Index: Alonso, Diego A.; Alonso, Emma; Najera, Carmen; Ramon, Diego J.; Yus, Miguel Tetrahedron, 1997 , vol. 53, # 13 p. 4835 - 4856

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Citation Number: 34

Abstract

Successive reaction of α-amidomethyl sulfones 7a, b, derived from primary amides, with n- butyllithium and primary alkyl bromides (CH2 CHCH2Br, CH2 CMeCH2Br, CH2 CBrCH2Br, CH CCH2Br, PhCH2Br, ButO2CCH2Br) at− 90° C yields, after hydrolysis, enamides 11. The same procedure applied to α-amidomethyl sulfones 7c, d derived from secondary amides and using different electrophiles [AcOD, D2O, EtI, CH2 CHCH2Br, ...