615576-90-4Relevant articles and documents
Design and synthesis of a new generation of 'NH'-Ni(II) complexes of glycine Schiff bases and their unprecedented C-H vs. N-H chemoselectivity in alkyl halide alkylations and Michael addition reactions
Ellis, Trevor K.,Soloshonok, Vadim A.
, p. 533 - 538 (2006)
Within this manuscript the synthesis of a new generation of Ni(II) complexes that contain a secondary rather than a tertiary amino group, as well as the unusual chemoselectivity, was demonstrated in alkyl halide alkylations and Michael addition reactions. The complete C-H chemoselectivity observed in these reactions suggests that coordination of nitrogen to a metal has a significant synthetic potential as protecting a group without the need of introducing a transient N-C substituent. These new complexes have also proven highly synthetically useful nucleophilic glycine equivalents for the simple and highly diastereoselective synthesis of β-substituted pyroglutamic acids via their reactions with chiral Michael acceptors. Georg Thieme Verlag Stuttgart.
NH-type of chiral Ni(ii) complexes of glycine Schiff base: Design, structural evaluation, reactivity and synthetic applications
Bergagnini, MacKenzie,Fukushi, Kazunobu,Han, Jianlin,Shibata, Norio,Roussel, Christian,Ellis, Trevor K.,Acena, Jose Luis,Soloshonok, Vadim A.
, p. 1278 - 1291 (2014/03/21)
The work being reported here deals with the design of a new type of "N-H" Ni(ii) complexes of glycine Schiff bases and study general aspects of their reactivity. It was confirmed that the presence of NH function in these Ni(ii) complexes does not interfere with the homologation of the glycine residue, rendering these derivatives of high synthetic value for the general synthesis of α-amino acids. In particular, the practical application of these NH-type complexes was demonstrated by asymmetric synthesis of various-substituted pyroglutamic acids via Michael addition reactions with chiral Michael acceptors.
Highly diastereoselective synthesis of new, carbostyril-based type of conformationally-constrained β-phenylserines
Ueki, Hisanori,Ellis, Trevor K.,Khan, Masood A.,Soloshonok, Vadim A.
, p. 7301 - 7306 (2007/10/03)
We have demonstrated that the readily available amido-keto compounds 5, with prearranged carbonyl and glycine moieties, under strongly basic conditions easily undergo complete and highly diastereoselective cyclization, affording a generalized and practical access to the conformationally constrained phenylserine derivatives 4. High chemical yields, virtually complete diastereoselectivity combined with the operational convenience of the experimental procedures render this method useful for preparation of these diastereomerically pure derivatives.
