181293-66-3Relevant academic research and scientific papers
Peptide catalyzed asymmetric conjugate addition reactions of aldehydes to nitroethylene - A convenient entry into γ2-amino acids
Wiesner, Markus,Revell, Jefferson D.,Tonazzi, Sandro,Wennemers, Helma
, p. 5610 - 5611 (2008/12/22)
The peptide H-d-Pro-Pro-Glu-NH2 is a highly effective catalyst for conjugate addition reactions between aldehydes and nitroethylene. Only 1 mol % of H-d-Pro-Pro-Glu-NH2 and a 1.5-fold excess of aldehyde with respect to nitroethylene suffice to obtain γ-nitroaldehydes and, after reduction, monosubstituted γ-nitroalcohols in excellent yields and optical purities. The products can be readily converted into γ2-amino acids, thereby opening an effective direct entry into this important class of compounds. Copyright
Enantioselective synthesis of 2-substituted 5-, 6- and 7-membered lactams via α-alkylation of their chiral N-dialkylamino derivatives
Enders, Dieter,Gr?bner, Robert,Raabe, Gerhard,Runsink, Jan
, p. 941 - 948 (2007/10/03)
2-Alkyl-substituted lactams 4 were synthesized in good overall yields and high enantiomeric purities (ee = 71-99%) by α-alkylation of chiral N-(dialkylamino)lactams 2 and subsequent reductive N-N bond cleavage of the resulting lactams 3 with lithium in liquid ammonia. The lactams 2, in turn, were prepared in good yields by cyclization of ω-chloroalkanohydrazides 1 with sodium hydride. Acidic hydrolysis of lactams 4 leads to γ-aminobutanoic acid (GABA) derivatives 5 (ee ≤ 99%). The absolute configuration was determined by polarimetry and an X-ray structure analysis of (S,S)-3e'.
