357428-17-2Relevant articles and documents
Structural features in the seven-membered vs. Fourteen-membered ring cyclization of hydroxyamido ketals derived from β-amino alcohols
Valade, Anne-Gaelle,Dugat, Denise,Jeminet, Georges,Royer, Jacques,Husson, Henri-Philippe
, p. 2041 - 2053 (2007/10/03)
Hydroxyamido ketals 1 and 3-12, prepared from β-amino alcohols, are obtained either as a single form with a trans (1 and 3-8) or cis (9) conformation in the R = H series or as two cis and trans rotamers in the R ≠ H series (10-12). - The cyclization of these compounds was studied under acidic conditions (PTSA) and over a well defined range of concentrations (c = 0.1-0.2 M). While cis amide 9 and mixtures of cis and trans rotamers 10-12 resulted practically exclusively in the formation of seven-membered ring lactams 22-25, trans compounds 1 and 3-8 afforded fourteen-membered ring bislactams 2, 13-18, the formation of which involves a dimerization. Macrocycles were obtained as three diastereomers in the chiral series 2, 13-16 and as two isomers in the achiral series 17 and 18. Nineteen macrocyclic bislactams have thus been synthesized.