189809-40-3Relevant academic research and scientific papers
N-Boc-α-tosylsarcosine ethyl ester: An α-amido sulfone for the regio- and stereoselective synthesis of protected γ,δ-unsaturated n-methyl-α- amino acids by palladium-catalyzed nucleophilic substitution
Alonso, Diego A.,Costa, Ana,Najera, Carmen
, p. 7943 - 7946 (2007/10/03)
N-Boc-α-tosylsarcosine ethyl ester (3) reacts under neutral conditions either with allylic carbonates or with vinyloxirane in the presence of a catalytic mount of Pd(PPh3)4 and dppe (5 mol%) to give regio- and stereoselectively the corresponding allylated products 5 and 6, respectively. Reductive desulfonylation of these compounds with Mg-MeOH affords the corresponding protected γ,δ-unsaturated N-methyl-α-amino acids 7 and 8.
α-Nitrogenated organolithium compounds from α-amidomethyl and α-aminomethyl sulfones
Alonso, Diego A.,Alonso, Emma,Najera, Carmen,Ramon, Diego J.,Yus, Miguel
, p. 4835 - 4856 (2007/10/03)
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 ≡ CCH
α-Nitrogenated organolithium compounds from N-(tosylmethyl)amides
Alonso, Diego A.,Alonso, Emma,Nájera, Carmen,Yus, Miguel
, p. 491 - 492 (2007/10/03)
Deprotonation of α-amido sulfones 7 with BunLi at -90°C followed by reaction with electrophiles leads, depending on the substitution on the amidic nitrogen to enamides 10 (secondary amides 7a,b) or functionalised α-amido sulfones 12 (tertiary amides 7c,d). Naphthalene-catalysed lithiation of tertiary α-amido sulfones 7c,d in the presence of electrophiles (Barbier conditions) at -78°C affords functionalised amides 13.
