222725-35-1Relevant articles and documents
Cross-metathesis of N-alkenyl peptoids with O- or C-allyl glycosides
Hu, Yun-Jin,Roy, Rene
, p. 3305 - 3308 (1999)
Cross-metathesis of several N-alkenyl-containing oligoglycines derivatives (peptoids) with protected O or C-allyl glycosides of N- acetylglucosamine, galactose, and mannose using Grubbs' ruthenium benzylidene catalyst (Cy3P)2Cl2Ru=CHPh (1) has been achieved in 40 to 52% yields.
Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion
Lawer, Aggie,Epton, Ryan G.,Stephens, Thomas C.,Palate, Kleopas Y.,Lodi, Mahendar,Marotte, Emilie,Lamb, Katie J.,Sangha, Jade K.,Lynam, Jason M.,Unsworth, William P.
, p. 12674 - 12683 (2020/09/17)
The outcome of ring-expansion reactions based on amino/hydroxyacid side-chain insertion is strongly dependent on ring size. This manuscript, which builds upon our previous work on Successive Ring Expansion (SuRE) methods, details efforts to better define the scope and limitations of these reactions on lactam and β-ketoester ring systems with respect to ring size and additional functionality. The synthetic results provide clear guidelines as to which substrate classes are more likely to be successful and are supported by computational results, using a density functional theory (DFT) approach. Calculating the relative Gibbs free energies of the three isomeric species that are formed reversibly during ring expansion enables the viability of new synthetic reactions to be correctly predicted in most cases. The new synthetic and computational results are expected to support the design of new lactam- and β-ketoester-based ring-expansion reactions.
Synthesis of cyclic dipeptides by ring-closing metathesis
Reichwein, John F.,Liskamp, Rob M. J.
, p. 2335 - 2344 (2007/10/03)
Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by 'amide-to-amide' cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or α,α-dichlorotoluene as an additive.
