Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: Structure-selectivity profiles and mechanistic studies
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
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)
Isothiourea-catalyzed enantioselective carboxy group transfer
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.
Joannesse, Caroline,Johnston, Craig P.,Concellon, Carmen,Simal, Carmen,Philp, Douglas,Smith, Andrew D.
supporting information; experimental part
p. 8914 - 8918
(2010/02/28)
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