1383537-23-2Relevant academic research and scientific papers
Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
Chen, Chien-Tien,Tsai, Cheng-Che,Tsou, Pei-Kang,Huang, Gou-Tao,Yu, Chin-Hui
, p. 524 - 529 (2016/12/30)
A pseudo-enantiomeric pair of optically switchable helicenes containing a catalytic 4-N-methylaminopyridine (MAP) bottom unit and a C2-symmetric, (10R,11R)-dimethoxymethyl-dibenzosuberane top template was synthesized. They underwent complementa
Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: Structure-selectivity profiles and mechanistic studies
Joannesse, Caroline,Johnston, Craig P.,Morrill, Louis C.,Woods, Philip A.,Kieffer, Madeleine,Nigst, Tobias A.,Mayr, Herbert,Lebl, Tomas,Philp, Douglas,Bragg, Ryan A.,Smith, Andrew D.
supporting information; experimental part, p. 2398 - 2408 (2012/03/27)
The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation. Copyright
Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes
Campbell, Craig D.,Concellon, Carmen,Smith, Andrew D.
experimental part, p. 797 - 811 (2011/08/06)
The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.
Isothiourea-catalyzed enantioselective carboxy group transfer
Joannesse, Caroline,Johnston, Craig P.,Concellon, Carmen,Simal, Carmen,Philp, Douglas,Smith, Andrew D.
supporting information; experimental part, p. 8914 - 8918 (2010/02/28)
Transferable skills: Enantiomerically pure isothioureas promote the 0-to C-carboxyl group transfer of oxazolyl carbonates with excellent levels of enantiocontrol (see scheme). The origin of the enantioselectivity of this process was probed mechanistically and rationalized computationally.
