181472-59-3Relevant academic research and scientific papers
α-Aminated methyllithium by DTBB-catalysed lithiation of a N- (chloromethyl) carbamate
Ortiz, Javier,Guijarro, Albert,Yus, Miguel
, p. 4831 - 4842 (2007/10/03)
The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate (1) with lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 2.5 mol %) in the presence of different electrophiles [Me3SiCl, (i)BuCHO, (t)BuCHO, PhCHO, 4-MeOC6H4CHO, (CH2)4CO, MeCO(n)Pr, Et2CO, MeCO(CH2)2CH=CH2, PhCOMe, PhCO(n)Bu, Ph2CO] in THF at -78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2. Carbamates 2 derived from carbonyl compounds are deprotected with hydrogen chloride (for aromatic aldehyde or ketone derivatives) or with a mixture of phenol and trimethylsilyl chloride (for aliphatic aldehyde derivatives) giving substituted 1,2-diols 4.
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.
O-tert-butyl-N-(chloromethyl)-N-methyl carbamate as a source of the MeNHCH2- synthon
Guijarro, Albert,Ortiz, Javier,Yus, Miguel
, p. 5597 - 5600 (2007/10/03)
The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate (1) with lithium powder and a catalytic amount of DTBB (2.5 mol %) in the presence of different electrophiles [Me3SiCl, Bu(i)CHO, Bu(t)CHO, PhCHO, (CH2)4CO, Et2CO, PhCOMe, Ph2CO] in THF at -78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2. As an example, the hydrolysis of compound 2e with hydrogen chloride affords easy deprotection of the amine functionality yielding the corresponding 1,2-aminoalcohol 3e.
